Organotin compounds and pesticides containing them

ABSTRACT

A compound of the formula: ##STR1## in which R 1  represents alkyl, cycloalkyl or aralkyl, R* represents fluorophenyl or trifluoromethylphenyl when R 1  is alkyl; R* represents dichlorophenyl, neopentyl, trimethylsilylmethyl, dimethylphenylsilylmethyl or a group of the formula: ##STR2## wherein R 2  represents halogen, trifluoromethyl, lower alkyl or lower alkoxy when R 1  is cycloalkyl; or R* represents 2-thienyl, 3-thienyl, neopentyl, trimethylsilylmethyl, imethylphenylsilylmethyl or a group of the formula: ##STR3## wherein R 3 , R 4  and R 5  independently represent hydrogen, halogen, trifluoromethyl, lower alkyl or lower alkoxy when R 1  is aralkyl, m represents 1 or 2, and X represents halogen, imidazolyl, triazolyl, phenylthio or a radical selected from the group consisting of: ##STR4## wherein R 6  represents alkyl, R 7  and R 8  independently represent lower alkyl and R 9  and R 10  independently represent hydrogen or lower alkyl when m is 1; or they independently represent oxygen, sulfur or a radical selected from: ##STR5## A process for preparing the compound (I) and a pesticidal composition containing the compound (I) are also provided.

This invention relates to novel asymmetric triorganotin compounds, to their preparation and to pesticidal compositions containing the novel compounds.

There exist a wide variety of pests which are parasitic on plants. Among them, mites (Acarina) do considerable damage to a wide range of crops and garden plants, which causes a serious problem in agricultural management. Since such phytophagous mites rapidly acquire a tolerance to pesticides, novel and efficient pesticides have continuously been sought.

Organic compounds which are known to be useful for controlling such mites include, for example, cyhexatin (Plictran®, U.S. Pat. No. 3,264,177) and fenbutatin oxide (Osadan®, U.S. Pat. No. 3,657,451). However, such known compounds have drawbacks that their pesticidal activities varies depending on species of pests, and that they do not inhibit a certain species of spider mites because of the acquired tolerance.

In view of the above, the present inventors have made extensive study on organotin compounds in order to find effective compounds exhibiting pesticidal activity, in particular, those effective to the spider mites which have already acquired a tolerance against the existing pesticides. As a result of the study, it has been found that the asymmetric triorganotin compounds of the formula (I) below exhibit an excellent pesticidal activity, in particular, to the spider mites exhibiting tolerance against the known organotin compounds.

Thus, the present invention provides assymmetric triorganotin compounds having pesticidal activity of the formula (I): ##STR6## in which R¹ represents alkyl, cycloalkyl or aralkyl, R* represents fluorophenyl or trifluoromethylphenyl when R¹ is alkyl; R* represents dichlorophenyl, neopentyl, trimethylsilylmethyl, dimethylphenylsilylmethyl or a group of the formula: ##STR7## wherein R² represents halogen, trifluoromethyl, lower alkyl or lower alkoxy when R¹ is cycloalkyl; or R* represents 2-thienyl, 3-thienyl, neopentyl, trimethylsilylmethyl, dimethylphenylsilylmethyl or a group of the formula: ##STR8## wherein R³, R⁴ and R⁵ independently represent hydrogen, halogen, trifluoromethyl, lower alkyl or lower alkoxy when R¹ is aralkyl, m represents 1 or 2, and X represents halogen, imidazolyl, triazolyl, phenylthio or a radical selected from the group consisting of: ##STR9## wherein R⁶ represents alkyl, R⁷ and R⁸ independently represent lower alkyl and R⁹ and R¹⁰ independently represent hydrogen or lower alkyl when m is 1; or they independently represent oxygen, sulfur or a radical selected from: ##STR10##

For purposes of the present invention, as disclosed and claimed herein, the following terms are as defined below.

The term "alkyl" refers to a straight or branched saturated hydrocarbon radical having one to twelve carbon atoms, including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, tert-pentyl, neopentyl, 1-methylbutyl, 1,2-dimethylbutyl, hexyl, heptyl, octyl, nonyl, decyl, and the like.

The term "lower alkyl" refers to an alkyl radical having less than six carbons, of the above defined alkyl.

The term "aralkyl" refers to an alkyl substituted by an aryl radical and includes benzyl, phenylethyl, phenylpropyl, methylbenzyl, neophyl, and the like.

The term "cycloalkyl" refers to a saturated hydrocarbon ring having three to ten carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and the like.

The term "halogen" means chloro, bromo, iodo and fluoro.

The term "pests" herein used should be considered to mean both insects and mites harmful to plants, especially phytophagous ones, and, the term "pesticides" or "pesticidal composition" to include insecticides and acaricides.

The process for the preparation of the compounds of the formula (I) will be detailed below.

The compounds (I) wherein X is halogen, which will hereinafter be referred to as compound (Ia), can be prepared according to the following Reaction Scheme I, whereas the other compounds (I) wherein X is other than halogen can be prepared from the compounds (Ia) according to the Reaction Schemes II to IV hereinafter described. ##STR11## In the above scheme, R* and R¹ are as previously defined, Hal, Y¹ and Y² are each chlorine, bromine or iodine, and n is 1 or 2, with the proviso that when n is 1, R* is a silicon-containing group and when n is 2, R* is an aryl or neopentyl group. The reactions are detailed below.

1st step

A compound (II) is reacted with an organotin halide (III) at a temperature from about 5° C. to 100° C. in a suitable solvent to yield an asymmetric tetraorganotin compound of the general formula (IV). Preferred solvents are ethers such as diethyl ether, dibutyl ether, tetrahydrofuran and the like.

The starting compound (II) may be conventionally prepared under the conditions usually employed for the preparation of a Grignard reagent.

The starting organotin halide of the general formula (III) wherein n is 2 can be represented by the formula:

    (R.sup.1).sub.2 Sn(Y.sup.2).sub.2

and may be prepared by redistribution reaction between a corresponding symmetric tetraorganotin compound of the formula:

    (R.sup.1).sub.4 Sn

wherein R¹ is as defined above, and a stannic halide according to known procedures. The asymmetric phenyldiorganotin halide, which corresponds to the starting compound of the formula (III) wherein n equals to 1 and has the formula:

    (R.sup.1).sub.2 Sn(Phe)Y.sup.2

is itself an objective compound of the present invention and, therefore, may be prepared from the aforementioned starting compound (III) wherein n is 2, in accordance with the Reaction Scheme I.

2nd step

Halogenation of the asymmetric tetraorganotin compound of the formula (IV) is convertionally carried out by direct addition of a gaseous halogen, or by addition of halogen dissolved in a suitable solvent, to a solution of the asymmetric tetraorganotin compound dissolved in the same solvent, while maintaining the reaction temperature at -50° C. to 30° C. Suitable solvents employed in the reaction include chloroform, carbon tetrachloride, benzene, toluene, heptane, hexane, and the like. Chloroform and carbon tetrachloride are especially preferred.

A preferred molar ratio of the asymmetric tetraorganotin compound (IV) and halogen is about 1:1. The reaction temperature is preferably maintained in the range of -10° C. to 10° C.

The reaction terminates when the addition of halogen or a halogen solution is complete. The reaction mixture is concentrated, and the desired compound is separated and purified by recrystallization, vacuum distillation or column chromatography, if necessary. The asymmetric triorganotin halides (Ia) thus prepared are liquid or solid at room temperature.

These halides (Ia) are easily converted to other objective compounds (I) of the invention, such as hydroxides, bis(asymmetric triorganotin)oxides and other various derivatives as shown in the following Reaction Schemes, by known procedures. ##STR12##

In the above schemes, R*, R¹, R⁶, R⁷, R⁸, R⁹, R¹⁰ and Hal are as defined previously, Az is 1,3-imidazol-1-yl or 1,2,4-triazol-1-yl. Desirable conditions for the reactions shown in the above schemes are known in the art, and disclosed, for example, by R. Inhan, Chemical Reviews, 459-539, 1960(October).

The compounds of formula (I) of the present invention exhibit an excellent pesticidal activity against phytophagous pests of various orders, such as Acarina, Lepidoptera, Hemiptera, Coleoptera, Orthoptera and Diptera. In particular, the compounds (I) exhibit an excellent inhibiting activity against a wide variety of acarina such as citrus red mite (Panonychus citri), European red mite (Panonychus ulmi), hawthorn spider mite (Tetranychus viennensis), Kanzawa spider mite (Tetranychus kanzawai), citrus flat mite (Brevipalpus lewisi), privet mite (Brevipalpus obovatus) and pink citrus rust mite (Aculops pelekassi). Moreover, the compounds (I) exert no harm, or only minor harm which is easily repaired, on crops and garden plants.

A certain class of spider mites, for example the kanzawa spider mite, shows resistance to known acaricides, cyhezatin (Plictran®, Dow Chemical Co., see U.S. Pat. No. 3,264,177), and fenbutatin oxide (Osadan®, Shell Oil Co., see U.S. Pat. No. 3,657,451). The compounds (I) of the invention, as stated before, show an excellent inhibiting activity even to the mites having resistance against such known acaricides.

Therefore, the present invention also provides a pesticidal composition which comprises as an active ingredient a compound of formula (I) together with a suitable carrier and/or adjuvant.

The pesticidal composition of the invention can be in any desirable form, such as wettable powders, emulsifiable concentrates, dusts or flowables, and prepared by mixing a compound (I) with one or more of non-phytotoxic carriers or adjuvants in accordance with conventional methods in the art. Such carriers and adjuvants include various liquid substances such as organic solvents and water, surfactants, granular or fine solid substances, and the like.

Wettable powders may be obtained by mixing a compound (I) with a solid carrier, such as clay, talc, white carbon, diatomaceous earth or bentonite, an ionic or nonionic emulsifier or dispersing agent, such as higher alkoxysulfonate, polyoxyehthylenesorbitan, alkylphenoxypolyethoxyethanol or lignosulfonate, and if required, wetting agents, protective colloid and the like. Emulsifiable concentrates may be obtained by dissolving a compound (I) in a suitable organic solvent and then adding thereto an appropriate surfactant. The emulsifiable concentrates can exist as water-in-oil concentrates or as oil-in-water concentrates having a high concentration comparable to a condensed mayonnaise.

The pesticidal compositions of the invention may be employed alone or after mixing with other acaricidal, insecticidal, or fungicidal compositions, plant growth regulator, fertillizer or the like.

The content of the compound (I) in the pesticidal composition in the form of wettable powder or emulsifiable concentrate is generally from 7 to 70 percent by weight, preferably from 20 to 50 percent by weight. The amount of the composition to be applied to loci of pests will vary depending on a number of factors, such as a method, season or locus of application, species of pests and crops, and the like. However, the composition is usually applied at the application rate of 200 to 600 liter per 10 are, after diluted to 500 to 10,000 fold, preferably 1,000 to 5,000 fold.

Dust compositions usually contain from 0.5 to 10 percent, preferably from 2 to 5 percent by weight of the compound (I), and are applied at application rate of from 3 to 5 kg per 10 are. Fine dust compositions contain the compounds (I) in the range of from 0.5 to 10 percent, preferably 1 to 5 percent by weight, and are applied at the rate in the range of from 1.5 to 5 kg per 10 are.

The following detailed Examples, Formulations and Experiments are presented by way of illustration of certain specific embodiments of the invention.

EXAMPLE 1 Dineophyl-metatrifluoromethylphenyltin fluoride (compound 1) (1) Dineophyl-di(metatrifluoromethylphenyl)tin

A 1,000 ml four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser was charged with magnesium (12.5 g, 0.51 mol) and flushed with nitrogen. Each 3 ml of a mixture of metatrifluoromethylphenyl bromide (113.4 g, 0.504 mol) and tetrahydrofuran (220 g) was portionwise added from the dropping funnel. The reaction occurred with fuming when the mixture was heated to 60°-70° C. While the temperature of the solution was maintained at 60° C., the solution of metatrifluoromethylphenyl bromide dissolved in tetrahydrofuran was added dropwise over about 2 hours.

After completion of the addition, the mixture was refluxed for 5 hours and then cooled to room temperature. Next, a solution of dineophyltin dichloride (85.6 g, 0.188 mol) dissolved in tetrahydrofuran (200 g) was dropwise added from a dropping funnel over 30 minutes, while maintaining the temperature at 10° to 20° C. After the addition, the mixture was kept at the reflux temperature for 7 hours. The mixture was then cooled to room temperature and hydrolyzed by the addition of a saturated aqueous ammonium chloride solution. The organic layer was separated, washed with water, filtered and concentrated under reduced pressure to yield brown viscous liquid. To this substance was added n-hexane (300 g) and activated clay (50 g) for decolorization. The mixture was filtered and concentrated under reduced pressure to obtain 118 g of dineophyl-di(metatrifluoromethylphenyl)tin as a colorless, clear and viscous liquid. Analysis by gas chromatography of the viscous liquid showed 95% purity. Tin content was 17.2% (theoretical: 17.6%).

(2) Dineophyl-metatrifluoromethylphenyltin fluoride

A 500 ml four-necked flask with a stirrer, a thermometer, a dropping funnel and a condenser was charged with dineophyl-dl(metatrifluoromethylphenyl)tin (80 g, 0.118 mol) obtained in Example 1-(1) and chloroform (200 g). A mixture of bromine (19 g, 0.216 gram atom) and chloroform (100 ml) was dropwise added from the dropping funnel over about 2.5 hours with stirring, while maintaining the temperature of the reaction mixture at -5° to 0° C. After completion of the addition, the mixture was allowed to warm to room temperature, filtered and concentrated under reduced pressure to give 72.2 g of dineophyl-metatrifluoromethylphenyltin bromide as a viscous liquid. The purity of the liquid was 93% based on a gas chromatography analysis. Crude dineophyl-metatrifluoromethylphenyltin bromide (72.2 g) thus prepared, benzen (120 g), potassium fluoride (14 g) and water (56 g) were charged into a 500 ml three-necked flask, and the mixture was refluxed for 2 hours. After completion of the reaction, the aqueous layer was separated off and the organic layer was washed with water, filtered and concentrated under reduced pressure. The resulting residue was crystallized from n-hexane at the temperature of -20° C. to obtain 33.8 g of dineophyl-metatrifluoromethylphenyltin bromide. This substance was a liquid at room temperature and has a refractive index of n³⁰ =1.5555. Tin content was 21.1% (theoretical: 21.6%).

EXAMPLE 2 Bis(dineophyl-metatrifluoromethylphenyltin)oxide (Compound 3)

Dineophyl-metatrifluoromethylphenyltin fluoride (13 g, 23.7 mmol) obtained in Example 1 was dissolved in benzene (60 g). To the resultant solution was added a 20% aqueous sodium hydroxide solution (7.2 g), and the mixture was allowed to react for one hour at a temperature between 75° C. and 80° C. After completion of the reaction, the aqueous layer was removed and the organic layer was washed with water and filtered. The benzene was distilled of from the organic layer under reduced pressure to yield 11.8 g of bis(dineophyl-metatrifluoromethylphenyltin)oxide as a pale-yellow viscous liquid. Refractive index: n³⁰ =1.5651; Tin content: 21.9% (theoretical: 22.1%).

EXAMPLE 3 Dineophyl-metatrifluoromethylphenyltin acetate (compound 5)

Bis(dineophyl-metatrifluoromethylphenyltin)oxide (6 g, 5.57 mmol) prepared in Example 2 was dissolved in n-hexane (30 g). To this solution was added glacial acetic acid (0.67 g, 11.16 mmol), and the mixture was heated at temperature of 70° to 75° C. for one hour to effect an azeotropic dehydration. After completion of the reaction, the mixture was filtered, and n-hexane was distilled off from the filtrate to obtain 6.4 g of dineophyl-metatrifluoromethylphenyltin acetate as a pale-yellow viscous liquid. Refractive index: n³⁰ =1.5465. Tin content: 20.1% (theoretical: 20.1%).

EXAMPLE 4 Dineophyl-metatrifluoromethylphenyltindimethyldithiocarbamate (compound 6)

Dineophyl-metatrifluoromethylphenyltin fluoride (10 g, 18.2 mmol) prepared in Example 1 was dissolved in benzene (50 g), and the resulting solution was added with a solution of sodium dimethyldithiocarbamate dihydrate (3.9 g, 21.8 mmol) dissolved in water (15.6 g). The mixture was heated at a temperature of from 75° to 80° C. for one hour. The aqueous layer was removed and the organic layer was washed with water and filtered. The filtrate was distilled to remove the benzene under reduced pressure and the resultant residue was recrystallized from petroleum ether to give 11.4 g of dineophyl-metatrifluoromethylphenyltindimethyldithiocarbamate as a white solid.

Mp: 96°-97° C. Tin content: 18.1% (theoretical: 18.2%).

EXAMPLE 5 Dineophyl-orthotrifluoromethylphenyltin chloride (compound 25)

Dineophyl-diorthotrifluoromethylphenyltin (113 g), a pale-yellow viscous liquid, was prepared in accordance with the teaching of Example 1 except that orthotrifluoromethylphenyl bromide (113.4 g, 0.502 mol), rather than metatrifluoromethylphenyl bromide, was used. Analysis of the resulting liquid by gas chromatography showed 96.3% purity. Tin content was 17.3%(theoretical: 17.6%).

Dineophyl-diorthotrifluoromethylphenyltin (80 g, 0.108 mol) obtained above was dissolved in chloroform (200 g). Chlorine gas (7.6 g, 0.216 gram atom) was then introduced into the resultant solution while keeping the temperature of the solution at between 0° C. and 5° C. The reaction mixture was then concentrated under reduced pressure and the resulting residue was recrystallized from methanol to yield 61.1 g of dineophyl-orthotrifluoromethylphenyltin chloride as a white solid. Analysis by gas chromatography of the solid indicated

97.3% purity.

Mp: 49°-50° C. Tin content: 21.0% (theoretical: 21.0%).

EXAMPLE 6 Bis(dineophyl-orthotrifluoromethylphenyltin)oxide (compound 16)

Dineophyl-orthotrifluoromethylphenyltin chloride (13.4 g, 23.7 mmol) obtained in Example 5 was hydrolyzed in accordance with the procedure described in Example 2 and the resultant product was recrystallized from n-hexane to give 12.1 g of bis(dineophyl-orthotrifluoromethylphenyltin)oxide.

Mp: 42°-44° C. Tin content: 21.8% (theoretical: 22.1%).

EXAMPLE 7 Dineophyl(orthotrifluoromethylphenyl)(1,2,4-triazole-1-yl)tin (compound 7)

Bis(dineophyl-orthotrifluoromethylphenyltin)oxide (6 g, 5.57 mmol) prepared in Example 6 and 1,2,4-triazole (0.77 g, 11.1 mmol) were dissolved in toluene (30 g), and the mixture was heated at 110°-112° C. for one hour to perform an azeotropic dehydration. The reaction mixture was filtered and distilled to remove the benzene, which gave 6.5 g of (dineophyl)(orthotrifluoromethylphenyl)(1,2,4-triazol-1-yl)tin as a pale-yellow viscous liquid.

Refractive index: n³⁰ =1.5690. Tin content: 20.7% (theoretical: 19.8%).

EXAMPLE 8 Bis(dineophyl-orthotrifluoromethylphenyltin)sulfate (compound 55)

Bis(dineophyl-orthotrifluoromethylphenyltin)oxide (2.7 g, 2.51 mmol) prepared in Example 6 was dissolved in benzene (30 ml). To the resultant solution was added a 50% aqueous sulfuric acid solution (5 ml) and the mixture was stirred at room temperature for 15 minutes. The aqueous layer was separated and removed, and the organic layer washed with water, filtered and concentrated under reduced pressure to give 2.8 g of bis(dineophyl-orthotrifluoromethylphenyltin)sulfate as a pale-yellow viscous liquid.

Refractive index: n³⁰ =1.5700. Tin content: 21.0% (theoretical: 20.5%).

EXAMPLE 9 Dineophyl-p-fluorophenyltin fluoride (compound 9)

Dineophyl-diparafluorophenyltin (100.9 g) was obtained as a colorless viscous liquid, in accordance with the teaching of Example 1-(1) except that parafluorophenyl bromide (89.3 g, 0.51 mol), rather than metatrifluoromethylphenyl bromide, was employed.

Gas chromatography analysis of this liquid showed 96.9% purity of the desired compound. Tin content was 20.6% (theoretical: 20.6%).

Dineophyl-di(parafluorophenyl)tin (62.1 g, 0.108 mol) prepared above was dissolved in chloroform (200 g). While the resulting solution was maintained at -15° to -20° C., chlorine gas (7.6 g, 0.216 gram atom,) was introduced. The mixture was then concentrated under reduced pressure to give 56 g of dineophyl-parafluorophenyltin chloride as a pale-yellow liquid. Gas chromatography analysis indicated 87.5% purity of the desired product.

A mixture consisting of the crude dineophyl-parafluorophenyltin chloride (50 g) and potassium fluoride (5.8 g, 0.1 mol) was heated for 2 hours in the presence of benzene (120 g) and water (23 g). The aqueous layer of the reaction mixture was removed, and the organic layer was washed with water, filtered and concentrated under reduced pressure. The residue thus obtained was crystallized from petroleum ether to give 38.5 g of dineophyl-parafluorophenyltin fluoride as a white solid.

Mp: 59°-62° C. Tin content: 23.2% (theoretical: 23.8%).

EXAMPLE 10 Bis(dineophyl-parafluorophenyltin)sulfide (compound 58)

Dineophyl-parafluorophenyltin fluoride (6 g, 12 mmol) obtained above was dissolved in benzene (30 ml). To this solution was added potassium sulfide (1 g, 17.7 mmol) dissolved in water (4 g) and the mixture was refluxed for 2 hours.

After the aqueous layer was separated and removed from the mixture, the organic layer washed with water and filtered. Evaporation of the benzene under reduced pressure yielded 6.4 g of bis(dineophyl-parafluorophenyltin)sulfide as a pale-yellow viscous liquid.

Refractive index: n³⁰ =1.6155. Tin content: 23.1% (theoretical: 23.9%).

EXAMPLE 11 Bis(dineophyl-parafluorophenyltin)oxide (compound 17)

Using dineophyl-parafluorophenyltin fluoride (15 g, 30 mmol) prepared in Example 9 and a 20% aqueous sodium hydroxide solution (9 g), bis(dineophyl-parafluorophenyltin)oxide was prepared in accordance with the procedure as described in Example 2, as a white solid.

Mp: 84°-86° C. Tin content: 24.5% (theoretical: 24.3%).

EXAMPLE 12 Dineophyl(parafluorophenyl)(1,3-imidazol-1-yl)tin (compound 54)

Bis(dineophyl-parafluorophenyltin)oxide (6 g, 6.14 mmol) prepared in Example 11 and 1,3-imidazole (0.83 g, 12.3 mmol) were dissolved in toluene (30 g) and the mixture was heated at 110°-112° C. for one hour to effect an azeotropic dehydration. Filteration of the reaction mixture and evaporation of the benzene gave a solid residue, which was crystallized from n-hexane to yield 5.1 g of dineophyl(parafluorophenyl)(1,3-imidazol-1-yl)tin.

Mp: 123°-127° C. Tin content: 21.2% (theoretical: 21.7%).

EXAMPLE 13 Dicyclohexyl-parafluorophenyltin fluoride (compound 14)

Dicyclohexyl-diparafluorophenyltin (85.2 g) was prepared in accordance with the procedure as described in Example 1(1) except that parafluorophenyl bromide (89.3 g, 0.51 mol) and dicyclohexyltin dichloride (76.9 g, 0.216 mol), rather than metatrifluoromethylphenyl bromide and dineophenyltin dichloride, were employed. Gas chromatography of the recrystallized product from isopropanol showed 98.6% purity.

Mp: 88°-90° C. Tin content: 25.1% (theoretical: 25.0%).

In accordance with the procedure as described in Example 1(2), the above product (20 g, 0.042 mol) was first reacted with bromine to produce crude dicyclohexyl-parafluorophenyltin bromide, which was then treated with sodium fluoride to yield 11.7 g of dicyclohexyl-parafluorophenyltin flouride as a white solid.

Mp: 234°-240° C. (dec.). Tin content: 29.9% (theoretical: 29.7%).

EXAMPLE 14 Dineophy-orthotrifluoromethylphenyltin isocyanate (compound 60)

Dineophyl-orthotrifluoromethylphenyltin chloride (6 g, 10.6 mmol) prepared in Example 5, sodium cyanate (1.1 g, 15.9 mmol) and acetone (40 g) were charged into a flask and the mixture was refluxed for 3 hours. The mixture was then added with benzene (50 g) and water (30 g). The aqueous layer was removed, and the organic layer was washed with water and filtered.

Evaporation of the benzene under reduced pressure gave 5.6 g of dineophyl-orthotritluoromethylphenyltin isocyanate as a colorless viscous liquid.

Refractive index: n³⁰ =1.5609. Tin content: 21.0% (theoretical: 20.7%).

EXAMPLE 15 Dineophyl-orthotrifluoromethylphenyltin isothiocyanate (compound 59)

Dineophyl-orthotrifluoromethylphenyltin chloride (6 g, 10.6 mmol) prepared in Example 5, potassium thiocyanate (1.5 g, 15.9 mmol), benzene (40 g) and water (10 g) were charged into a flask and the mixture was refluxed for 2 hours. The aqueous layer was removed and the organic layer was washed with water and filtered. Evaporation of the benzene under reduced pressure gave 6.0 g of dineophyl-orthotrifluoromethylphenyltin isothiocyanate as a colorless viscous liquid.

Refractive index: n³⁰ =1.5787. Tin content: 20.5% (theoretical: 20.2%).

EXAMPLE 16 Dineophyl-orthotrifluoromethylphenyltin methylsulfide (compound 67)

Dineophyl-orthotrifluoromethylphenyltin chloride (6 g, 10.6 mmol) prepared in Example 5, a 15% aqueous sodium methylsulfide solution (7.4 g, 15.9 mmol) and benzene (40 g) were charged into a flask and the mixture was refluxed for 2 hours. The aqueous layer was removed and the organic layer was washed with water and filtered. Evaporation of the benzene under reduced pressure yielded 4.6 g of dineophylorthotrifluoromethylphenyltin methylsulfide as a colorless viscous liquid.

Refractive index: n³⁰ =1.5804. Tin content: 20.9% (theoretical: 20.6%).

EXAMPLE 17 Dineophyl-orthotrifluoromethylphenyltin phenoxide (compound 68)

Bis(dineophyl-orthotrifluoromethylphenyltin)oxide (6 g, 5.6 mmol) prepared in Example 6, phenol (1.0 g, 11.2 mmol) and toluene (40 g) were charged into a flask and the mixture was allowed to react substantially in accordance with the procedure described in Example 7. Evaporation of the toluene followed by recrystallization of the resulting residue from petroleum ether yielded 4.4 g of dineophyl-orthotrifluoromethylphenyltin phenoxide as a white solid.

Mp: 69°-71° C. Tin content: 19.1% (theoretical: 19.0%).

EXAMPLE 18 Dineophyl-orthotrifluoromethylphenyltin phenylsulfide (compound 69)

A mixture of bis(dineophyl-orthotrifluoromethylphenyltin)oxide (6.0 g, 5.6 mmol) prepared in Example 6, thiophenol (1.2 g, 11.2 mmol) and toluene (40 g) was treated with the procedure described in Example 7. The product was recrystallized from n-hexane to obtain 5.2 g of dineophylorthotrifluoromethylphenyltin phenylsulfide as a white solid.

Mp: 81°-82° C. Tin content: 18.7% (theoretical: 18.6%).

EXAMPLE 19 S-(Dineophyl-orthotrifluoromethylphenyltin)O,O-diethyldithiophosphate (compound 71)

In substantial accordance with the procedure described in Example 7, a mixture of bis(dineophyl-orthotrifluoromethylphenyltin)oxide (6.8 g, 6.4 mmol) prepared in Example 6, O,O-diethyldithiophosphate (2.2 g, 12.8 mmol) and toluene (40 g) was reacted to provide 8.0 g of S-(dineophylorthotrifluoromethylphenyltin)O,O-diethyldithiophosphate as a colorless viscous liquid.

Refractive index: n³⁰ =1.5759.

EXAMPLE 20 Dineophyl(4-chloro-3-trifluoromethylphenyl)tin bromide (compound 74)

Dineophyl-di(4-chloro-3-trifluoromethylphenyl)tin (125.8 g), a pale-yellow viscous liquid, was prepared in substantial accordance with the procedure described in Example 1-(1) except that 4-chloro-3-trifluoromethylphenyl bromide (131.0 g, 0.504 mol), rather than metatrifluoromethylphenyl bromide, was employed. Gas chromatography analysis of this liquid showed 98.5% purity. Tin content was 15.6% (theoretical: 15.9%).

Following the procedure described in Example 1-(2), dineophyl-di(4-chloro-3-trifluoromethylphenyl)tin (87.8 g, 0.118 mol) obtained above was then reacted with bromine to obtain a pale-yellow solid (79.2 g). This solid was recrystallized from methanol (200 g) to give 65.7 g of dineophyl-4-chloro-3-trifluoromethylphenyltin bromide as a white solid. Gas chromatography analysis of this solid showed 99.0% purity. Mp: 72°-74° C. Tin content: 18.3% (theoretical: 18.4%).

EXAMPLE 21 Dineophyl-2,4-difluorophenyltin fluoride (compound 79)

Dineophyl-di(2,4-difluorophenyl)tin (107.9 g), a colorless viscous liquid, was prepared according to the procedure described in Example 1-(1) except that 2,4-difluorophenyl bromide (98.4 g, 0.51 mol), rather than metatrifluoromethylphenyl bromide, was used. Gas chromatography analysis of this liquid showed 95.5% purity. Tin content was 19.0% (theoretical: 19.4%).

Next, following the procedure described in Example 1(2), the above product (72.1 g, 0.118 mol) was reacted with bromine to obtain crude dineophyl-2,4-difluorophenyltin bromide, which was then treated with sodium fluoride. Recrystallization of the resultant product from n-hexane gave 30.6 g of dineophyl-2,4-difluorophenyltn fluoride as a white solid.

Mp: 60°-65° C. Tin content: 22.6% (theoretical: 22.9%).

EXAMPLE 22 Dineophyl-2,4,5-trifluorophenyltin chloride (compound 92)

Dineophyl-di(2,4,5-trifluorophenyl)tin (113.1 g), a pale-yellow viscous liquid, was prepared in substantial accordance with the procedure described in Example 1 (1) except that 2,4,5-trifluorophenyl bromide (105.9 g, 0.502 mol), rather than metatrifluoromethylphenyl bromide, was employed. Gas chromatography analysis of this liquid showed 96.0% purity. Tin content was 17.8% (theoretical: 18.3%).

The above product (76.4 g, 0.118 mol) was then reacted with chlorine and the reaction mixture was worked up in substantial accordance with the procedure described in Example 5. Recrystallization of the product from n-hexane gave 39.3 g of dineophyl-2,4,5-trifluorophenyltin chloride as a white solid. Gas chromatography analysis of this solid showed 99.9% purity.

Mp: 65°-67° C. Tin content: 21.7% (theoretical: 21.5%).

EXAMPLE 23 Dineophyl-parachlorophenyltin fluoride (compound 108)

Dineophyl-di(parachlorophenyl)tin (107.5 g), a colorless viscous liquid, was prepared in substantial accordance with the procedure described in Example 1 except that metachlorophenyl bromide (97.4 g, 0.51 mol), rather than metatrifluoromethylphenyl bromide, was employed. Gas chromatography analysis of this liquid indicated 97.5% purity. Tin content was 19.1% (theoretical: 19.5%).

In substantial accordance with the procedure described in Example 1(2), the above product (71.8 g, 0.118 mol) was reacted with bromine to obtain crude dineophyl-metachlorophenyltin bromide, which was then reacted with sodium fluoride. The resulting product was recrystallized from n-hexane to provide 32.7 g of dineophyl-metachlorophenyltin fluoride as a white solid.

Mp: 104°-105° C. Tin content: 23.0% (theoretical: 23.0%).

EXAMPLE 24 Dineophyl-phenyltin fluoride (compound 144)

Dineophyl-diphenyltin (108.9 g), a colorless viscous liquid, was prepared in substantial accordance with the procedure described in Example 1-(1) except that phenyl bromide (78.8 g, 0.502 mol), rather than metatrifluoromethylphenyl bromide, was employed. Gas chromatography analysis of this liquid showed 97.8% purity. Tin content was 21.7% (theoretical: 22.0%).

Dineophyl-phenyltin fluoride (39.6 g), a white solid, was prepared using the above product (80 g, 0.128 mol) as described in Example 1(2).

Mp: 37°-40° C. Tin content: 24.9% (theoretical: 24.7%).

EXAMPLE 25 Dineophyl-orthomethoxyphenyltin chloride (compound 133)

Dineophyl-di(orthomethoxyphenyl)tin (105.9 g), a colorless viscous liquid, was prepared in substantial accordance with the procedure described in Example 1(1) except that orthoanisyl bromide (93.8 g, 0.502 mol), rather than metatrifluoromethylphenyl bromide, was employed. Gas chromatography analysis of this liquid showed 96.5% purity. Tin content was 19.5% (theoretical: 19%).

Dineophyl-orthomethoxyphenyltin chloride (30.1 g), a white solid, was prepared using the above product (70.7 g, 0.118 mol) and chlorine in the manner as described in Example 5. Gas chromatography analysis of this solid showed 99.5% purity.

Mp: 69°-72° C. Tin content: 22.7% (theoretical: 22.5%).

EXAMPLE 26 Dineophyl-3-thienyltin fluoride (compound 215) (1) Dineophyl-di(3-thienyl)tin

A 1,000 ml four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser was charged with 3-thienyl bromide (75 g, 0.0461 mol) and absolute ether (200 g). n-Butyl lithium (185.3 g) (15% solution in n-hexane) was added in dropwise fashion from the dropping funnel while maintaining the temperature of the reaction mixture at below -50° C. After completion of the addition, the reaction mixture was stirred for about 10 minutes at below -50° C. and then added with a solution of dineophyltin chloride (73.5 g, 0.161 mol) dissolved in tetrahydrofuran (140 g) through the dropping funnel at -50° to -60° C. over about 30 minutes. After completion of the addition, the mixture was stirred for about 2 hours at that temperature, allowed to warm to room temperature and stirred for about additional one hour. The reaction mixture was then hydrolyzed by the addition of water (120 ml). The organic layer was separated, added with hexane (200 g), washed with water, filtered and concentrated under reduced pressure to yield a brown viscous liquid. To this liquid were added n-hexane (300 g) and activated clay (50 g) for discolorization. The mixture was filtered and concentrated under reduced pressure to obtain 81.7 g of dineophyl-di(3-thienyl)tin as a colorless, transparent and viscous liquid. Gas chromatography analysis of this liquid showed 95.0% purity. Tin content was 21.0% (theoretical: 21.6%).

(2) Dineophyl-3-thienyltin fluoride

In substantial accordance with the procedure described in Example 1(2), dineophyl-di(3-thienyl)tin (80 g, 0.145 mol) obtained above was reacted with bromine to give crude dineophyl-3-thienyltin bromide, which was then reacted with sodium fluoride. The resulting product was recrystallized from n-hexane to provide 21.5 g of dineophyl-3-thienyltin fluoride as a white solid.

Mp: 85°-90° C. Tin content: 24.7% (theoretical: 24.4%).

EXAMPLE 27 Dicyclohexyl-paratrifluoromethylphenyltin chloride (compound 164)

Crude dicyclohexyl-di(paratrifluoromethylphenyl)tin (101.7 g), a white solid, was prepared in accordance with the procedure described in Example 1(1) except that paratrifluoromethylphenyl bromide (113.4 g, 0.504 mol) and dicyclohexyltin dichloride (66.9 g, 0.188 mol), rather than metatrifluoromethylphenyl bromide and dineophyltin dichloride, were employed. Gas chromatography analysis of this solid indicated 93.3% purity.

In substantial accordance with the procedure described in Example 5, the above product (60 g, 0.105 mol) was then reacted with chlorine and the resulting mixture was worked up to yield 31.5 g of dicyclohexyl-paratrifluoromethylphenyltin chloride as a white solid. Gas chromatography analysis of this solid indicated 99.0% purity.

Mp: 74°-75° C. Tin content: 25.8% (theoretical: 25.5%).

EXAMPLE 28 Bis(dicyclohexyl-paratrifluoromethylphenyltin)oxide (compound 165)

Dicyclohexyl-paratrifluoromethylphenyltin chloride (15.0 g, 32.2 mmol) prepared in Example 27 was treated in the manner as described in Example 6 to provide 11.3 g of bis(dicyclohexyl-paratrifluoromethylphenyltin)oxide as a white solid.

Mp: 86°-89° C. Tin content: 26.8% (theoretical: 27.1%).

EXAMPLE 29 Dicyclohexyl-paratrifluoromethylphenyltin-n-butylthioglycolate (compound 167)

Bis(dicyclohexyl-paratrifluoromethylphenyltin)oxide (6 g, 16.8 mmol) prepared in Example 28 and n-butyl thioglycolate (2.0 g, 13.6 mmol) were dissolved in toluene (30 g) and the mixture was heated at 110°-112° C. for one hour to effect an azeotropic dehydration. Evaporation of the toluene under reduced pressure gave 7.8 g of pale-yellow liquid.

Refractive index: n³⁰ =1.5337. Tin content: 20.4% (theoretical: 20.6%).

EXAMPLE 30 Dicyclohexyl-3,4-dichlorophenyltin fluoride (compound 190)

Dicyclohexyl-di(3,4-dichlorophenyl)tin (101.9 g), a colorless viscous liquid, was prepared in substantial accordance with the procedure described in Example 1(1) except that 3,4-dichlorophenyl bromide (113.8 g, 0.504 mol) and dicyclohexyltin dichloride (66.9 g, 0.188 mol), rather than metatrifluoromethylphenyl bromide and dineophyltin dichloride, were employed. Gas chromatography analysis of this liquid showed 95.9% purity. Tin content was 20.2% (theoretical: 20.6%).

Dicyclohexyl-di(3,4-dichlorophenyl)tin (86.5 g, 0.150 mol) prepared above was allowed to react and the resulting mixture was worked up, as described in Example 1-(2), to obtain 35.5 g of dicyclohexyl-3,4-dichlorophenyltin fluoride as a white solid.

Mp: 193° C. Tin content: 26.0% (theoretical: 26.4%).

EXAMPLE 31 Dicyclohexyl-paratolyltin chloride (compound 197)

Dicyclohexyl-di(paratolyl)tin (82.5 g), a pale-yellow viscous liquid, was prepared in substantial accordance with the procedure described in Example 1(1) except that paratolyl bromide (86.2 g, 0.504 mol) and dicyclohexyltin dichloride (66.9 g, 0.188 mol), rather than metatrifluoromethylphenyl bromide and dineophyltin dichloride, were employed. Gas chromatography analysis of this liquid showed 94.5% purity. Tin content was 24.7% (theoretical: 25.4%).

The above product (70 g, 0.150 mol) was then allowed to react with chlorine and the resulting mixture was worked up, as described in Example 5, to obtain 34.5 g of dicyclohexyl-paratolyltin chloride as a colorless viscous liquid. Gas chromatography analysis of this liquid showed 98.4% purity.

Refractive index: n³⁰ =1.5705. Tin content: 28.6% (theoretical: 28.8%).

EXAMPLE 32 Dicyclohexyl-trimethylsilylmethyltin chloride (compound 232) (1) Dicyclohexyl-phenyltin chloride

Dicyclohexyl-di(phenyl)tin (155.2 g), a white solid, was prepared in substantial accordance with the procedure described in Example 1(1) except that phenyl bromide (156.2 g, 1.008 mol) and dicyclohexyltin dichloride (133.8 g, 0.376 mol), rather than metatrifluoromethylphenyl bromide and dineophyltin dichloride, were employed. Gas chromatography analysis of this solid showed 94.9% purity.

The above product (150.8 g, 0.343 mol) was then allowed to react with chlorine and the resultant mixture was worked up as described in Example 5. Recrystallization of the product from n-hexane gave 86.0 g of dicyclohexyl-phenyltin chloride as a white solid. Gas chromatography analysis of this solid showed 98.8% purity.

Mp: 50°-52° C. Tin content: 30.2% (theoretical: 29.9%).

(2) Dicyclohexyl-trimethylsilylmethyltin chloride

Dicyclohexyl-phenyl-trimethylsilylmethyltin (79.4 g), a colorless viscous liquid, was prepared as described in Example 1(1). Using dicyclohexyl-phenyltin chloride (74.7 g, 0.188 mol) obtained above and trimethylsilylmethyl chloride (30.8 g, 0.251 mol) instead of dineophyltin dichloride and metatrifluoromethylphenyl bromide respectively. In this example, 6.1 g (0.251 mol) of magnesium and 110 g of tetrahydrofuran were employed. Gas chromatography analysis of this liquid showed 97.5% purity.

In the manner as taught in Example 5, the above product (48.5 g, 0.108 mol) was reacted with chlorine, and the resultant mixture was concentrated. The residue was recrystallized from n-hexane to yield 35.2 g of dineophyl-trimethylsilylmethyltin chloride as a white solid. Gas chromatography analysis of this solid showed 99.0% purity.

Mp: 74° C.

EXAMPLE 33 Bis(dicyclohexyl-trimethylsilylmethyltin)oxide (compound 233)

Dicyclohexyl-trimethylsilylmethyltin chloride (25.3 g, 0.062 mol) prepared in Example 32 was allowed to react and the resultant mixture was worked up, as described in Example 2, to provide 21.2 g of bis(dicyclohexyl-trimethylsilylmethyltin)oxide as a white solid. Mp: 151°-153° C.

EXAMPLE 34 o-(Dicyclohexyl-trimethylsilylmethyltin) o,o-dibutylphosphate (compound 237)

Bis(dicyclohexyl-trimethylsilylmethyltin)oxide (6.8 g, 8.9 mmol), o,o-dibutylphosphate (3.7 g, 17.8 mmol) and toluene (40 g) were allowed to react as described in Example 7. Evaporation of the toluene from the mixture and recrystallization of the residue from methanol/acetonitrile gave 8.3 g of o-(dicyclohexyl-trimethylsilylmethyltin) o,o-dibutylphosphate as a white solid. Mp: 130°-132° C.

In substantial accordance with the procedures as taught in the above examples, a variety of organotin compounds (I) of the invention were prepared. Physicochemical properties of the compounds are listed in Table 1.

In Table 1, the following abbreviations were employed:

Me: methyl

Et: ethyl

Bu: butyl

Oct: octyl

Phe: phenyl

Ac: acetyl

Tin content in parenthesis represents theoretical amount.

                                      TABLE 1-1                                    __________________________________________________________________________      ##STR13##                                                                                                       Physical property                            Com-                                                   Tin GLC                 pound                                      m.p. or     content                                                                            purity              No.  R.sup.2 R.sup.1                                                                              m X            Appearance                                                                              b.p.    n.sup.30                                                                           (%) (%)                 __________________________________________________________________________     1    m-CF.sub.3                                                                             Neophyl                                                                              1 F            Viscous liquid   1.5555                                                                             21.1                                                                           (21.6)                  2    p-F     n-Butyl                                                                              1 F            White solid                                                                             205-210° C.                                                                         34.2                                                                           (34.4)                  3    m-CF.sub.3                                                                             Neophyl                                                                              2 O            Viscous liquid   1.5651                                                                             21.9                                                                           (22.1)                  4    m-CF.sub.3                                                                             Neophyl                                                                              1 Cl           Colorless liquid 1.5591                                                                             21.2                                                                               99.3                                                                       (21.0)                  5    m-CF.sub.3                                                                             Neophyl                                                                              1 OCOMe        Viscous liquid   1.5465                                                                             20.1                                                                           (20.1)                  6    m-CF.sub.3                                                                             Neophyl                                                                              1 SSCN(Me).sub.2                                                                              White solid                                                                             96-97° C.                                                                           18.1                                                                           (18.2)                  7    o-CF.sub.3                                                                             Neophyl                                                                              1 Triazolyl    Viscous liquid   1.5690                                                                             20.7                                                                           (19.8)                  8    o-CF.sub.3                                                                             Neophyl                                                                              1 F            White solid                                                                             38-40° C.                                                                           21.0                                                                           (21.6)                  9    p-F     Neophyl                                                                              1 F            White solid                                                                             59-62° C.                                                                           23.2                                                                           (23.8)                  10   m-F     Neophyl                                                                              1 F            White solid                                                                             35-38° C.                                                                           23.3                                                                           (23.8)                  11   o-CF.sub.3                                                                             n-Butyl                                                                              1 F            White solid                                                                             105-111° C.                                                                         29.2                                                               (decomp.)   (29.9)                  12   m-CF.sub.3                                                                             n-Butyl                                                                              1 F            White solid                                                                             142° C.                                                                             29.2                                                               (decomp.)   (29.9)                  13   p-F     n-Octyl                                                                              1 F            White solid                                                                             57-60° C.                                                                           26.0                                                                           (25.8)                  14   p-F     Cyclohexyl                                                                           1 F            White solid                                                                             235-240° C.                                                                         29.9                                                               (decomp.)   (29.7)                  15   m-CF.sub.3                                                                             Cyclohexyl                                                                           1 F            White solid                                                                             280° C.                                                                             26.8                                                               (decomp.)   (26.4)                  16   o-CF.sub.3                                                                             Neophyl                                                                              2 O            White solid                                                                             42-44° C.                                                                           21.8                                                                           (22.1)                  17   p-F     Neophyl                                                                              2 O            White solid                                                                             84-86° C.                                                                           24.5                                                                           (24.3)                  18   m-F     Neophyl                                                                              2 O            White solid                                                                             37-39° C.                                                                           24.6                                                                           (24.3)                  19   o-CF.sub.3                                                                             n-Butyl                                                                              2 O            Colorless liquid 1.5031                                                                             31.3                                                                           (32.2)                  20   m-CF.sub.3                                                                             n-Butyl                                                                              2 O            Colorless liquid 1.4939                                                                             30.8                                                                           (30.7)                  21   p-F     n-Butyl                                                                              2 O            Colorless liquid 1.5285                                                                             35.3                                                                           (35.3)                  22   p-F     n-Octyl                                                                              2 O            Colorless liquid 1.5084                                                                             26.5                                                                           (26.5)                  23   p-F     Cyclohexyl                                                                           2 O            White solid                                                                             69-72° C.                                                                           30.4                                                                           (30.6)                  24   m-CF.sub.3                                                                             n-Butyl                                                                              1 Br           Colorless liquid                                                                         170-172° C./                                                                   1.5109                                                                             25.5                                                                               96.3                                                              7 mmHg   (25.9)                  25   o-CF.sub.3                                                                             Neophyl                                                                              1 Cl           White solid                                                                             49-50° C.                                                                           21.0                                                                               97.3                                                                       (21.0)                  26   p-F     Neophyl                                                                              1 Cl           Colorless liquid 1.5824                                                                             23.0                                                                               99.3                                                                       (23.0)                  27   m-F     Neophyl                                                                              1 Cl           Colorless liquid 1.5829                                                                             23.1                                                                               97.1                                                                       (23.0)                  28   o-CF.sub.3                                                                             n-Butyl                                                                              1 Cl           Colorless liquid 1.5005                                                                             28.1                                                                               95.0                                                                       (28.7)                  29   p-F     n-Butyl                                                                              1 Cl           Colorless liquid                                                                         160-165° C./                                                                   1.5249                                                                             32.2                                                                               96.2                                                             4-6 mmHg  (32.7)                  30   p-F     n-Octyl                                                                              1 Cl           Colorless liquid 1.5041                                                                             25.1                                                                               96.2                                                                       (25.0)                  31   p-F     Cyclohexyl                                                                           1 Cl           White solid                                                                             52-55° C.                                                                           28.6                                                                               98.7                                                                       (28.6)                  32   m-CF.sub.3                                                                             Cyclohexyl                                                                           1 Cl           Pale yellow liquid                                                                              1.5352                                                                             24.5                                                                               98.4                                                                       (25.5)                  33   o-CF.sub.3                                                                             Neophyl                                                                              1 OCOMe        Viscous liquid   1.5535                                                                             20.0                                                                           (25.1)                  34   p-F     Neophyl                                                                              1 OCOMe        Viscous liquid   1.5669                                                                             22.5                                                                           (22.0)                  35   m-F     Neophyl                                                                              1 OCOMe        Viscous liquid   1.5675                                                                             22.4                                                                           (22.0)                  36   o-CF.sub.3                                                                             n-Butyl                                                                              1 OCOMe        Viscous liquid   1.4851                                                                             26.5                                                                           (27.2)                  37   m-CF.sub.3                                                                             n-Butyl                                                                              1 OCOMe        Colorless solid                                                                         75-78° C.                                                                           27.3                                                                           (27.2)                  38   p-F     n-Butyl                                                                              1 OCOMe        Colorless solid                                                                         83-85° C.                                                                           31.1                                                                           (30.7)                  39   p-F     n-Octyl                                                                              1 OCOMe        Colorless solid                                                                         27-30° C.                                                                           24.0                                                                           (23.8)                  40   p-F     Cyclohexyl                                                                           1 OCOMe        Colorless solid                                                                         48-50° C.                                                                           27.5                                                                           (27.0)                  41   o-CF.sub.3                                                                             Neophyl                                                                              1 SSCN(Me).sub. 2                                                                             Colorless solid                                                                         102-105° C.                                                                         18.5                                                                           (18.3)                  42   p-F     Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Colorless solid                                                                         74-76° C.                                                                           19.6                                                                           (20.2)                  43   m-F     Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid                20.3                                                                           (20.2)                  44   o-CF.sub.3                                                                             n-Butyl                                                                              1 SSCN(Me).sub.2                                                                              Colorless solid                                                                         28-30° C.                                                                           23.9                                                                           (23.8)                  45   m-CF.sub.3                                                                             n-Butyl                                                                              1 SSCN(Me).sub.2                                                                              Yellow liquid    1.5611                                                                             23.8                                                                           (23.8)                  46   p-F     n-Butyl                                                                              1 SSCN(Me).sub.2                                                                              Pale yellow liquid                                                                              1.5880                                                                             26.5                                                                           (26.5)                  47   p-F     n-Octyl                                                                              1 SSCN(Me).sub.2                                                                              Pale yellow liquid                                                                              1.5510                                                                             21.2                                                                           (21.2)                  44   p-F     Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Colorless solid                                                                         101-105° C.                                                                         24.2                                                                           (23.7)                  49   p-F     Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Colorless solid                                                                         134-137° C.                                                                         21.0                                                                           (21.6)                  50   m-F     Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Colorless solid                                                                         154-157° C.                                                                         21.6                                                                           (21.6)                  51   p-F     n-Butyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Colorless solid                                                                         68-72° C.                                                                           28.7                                                                           (30.0)                  52   m-CF.sub.3                                                                             n-Butyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Viscous liquid   1.5205                                                                             26.0                                                                           (26.6)                  53   p-F     n-Octyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Viscous liquid   1.5220                                                                             22.8                                                                           (23.4)                  54   p-F     Neophyl                                                                              1 1,3-Imidazol-1-yl                                                                           Colorless solid                                                                         123-127° C.                                                                         21.2                                                                           (21.7)                  55   o-CF.sub.3                                                                             Neophyl                                                                              2 OSO.sub.2 O  Viscous liquid   1.5700                                                                             21.0                                                                           (20.5)                  56   p-F     Neophyl                                                                              2 OSO.sub.2 O  Viscous liquid   1.5961                                                                             23.0                                                                           (22.5)                  57   o-CF.sub.3                                                                             Neophyl                                                                              2 S            Viscous liquid   1.6029                                                                             20.9                                                                           (21.7)                  58   p-F     Neophyl                                                                              2 S            Viscous liquid   1.6155                                                                             23.1                                                                           (23.9)                  59   o-CF.sub.3                                                                             Neophyl                                                                              1 NCO          Liquid           1.5787                                                                             20.5                                                                           (20.2)                  60   p-F     Neophyl                                                                              1 NCS          Liquid           1.5609                                                                             21.0                                                                           (20.7)                  61   o-CF.sub.3                                                                             Neophyl                                                                              1                                                                                 ##STR14##   Liquid           1.5279                                                                              (16.3)16.5             62   o-CF.sub.3                                                                             Neophyl                                                                              1                                                                                 ##STR15##   Liquid           1.5414                                                                              (18.8)18.6             63   o-CF.sub.3                                                                             Neophyl                                                                              2                                                                                 ##STR16##   Solid    128-131° C.                                                                          (17.6)17.5             64   o-CF.sub.3                                                                             Neophyl                                                                              1 SCH.sub.2 COOn-Bu                                                                           Liquid           1.5632                      65   o-CF.sub.3                                                                             Neophyl                                                                              1 SCH.sub.2 COOn-Oct                                                                          Liquid           1.5499                      66   o-CF.sub.3                                                                             Neophyl                                                                              1 1,3-Imidazol-1-yl                                                                           Viscous liquid   1.5686                                                                             19.7                                                                           (19.9)                  67   o-CF.sub.3                                                                             Neophyl                                                                              1 SMe          Viscous liquid   1.5804                                                                             20.9                                                                           (20.6)                  68   o-CF.sub.3                                                                             Neophyl                                                                              1 Phenoxy      Solid    69-71° C.                                                                           19.1                                                                           (19.0)                  69   o-CF.sub. 3                                                                            Neophyl                                                                              1 Phenylthio   Solid    81-82° C.                                                                           18.7                                                                           (18.6)                  70   o-CF.sub.3                                                                             Neophyl                                                                              1                                                                                 ##STR17##   Solid    63-69° C.                    71   o-CF.sub.3                                                                             Neophyl                                                                              1                                                                                 ##STR18##   Viscous liquid   1.5759                      72   3-CF.sub.3                                                                             Neophyl                                                                              1 F            Solid    50-56° C.                                                                           20.6                         4-Cl                                              (20.3)                  73   3-CF.sub.3                                                                             Neophyl                                                                              1 Cl           Solid    69-71° C.                                                                           20.9                                                                               99.0                     4-Cl                                              (19.8)                  74   3-CF.sub.3                                                                             Neophyl                                                                              1 Br           Solid    72-74° C.                                                                           18.3                                                                               97.0                     4-Cl                                              (18.4)                  75   3-CF.sub.3                                                                             Neophyl                                                                              2 O            Solid    58-61° C.                                                                           20.4                         4-Cl                                              (20.7)                  76   3-CF.sub.3                                                                             Neophyl                                                                              1 OAc          Solid    60-62° C.                                                                           19.2                         4-Cl                                              (19.0)                  77   3-CF.sub.3                                                                             Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    86-88° C.                                                                           17.6                         4-Cl                                              (17.3)                  78   3-CF.sub.3                                                                             Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    159-161° C.                                                                         18.7                         4-Cl                                              (18.8)                  79   2,4-Difluoro                                                                           Neophyl                                                                              1 F            Solid    60-63° C.                                                                           22.6                                                                           (22.9)                  80   2,4-Difluoro                                                                           Neophyl                                                                              1 Cl           Liquid           1.5730                                                                             21.9                                                                               98.1                                                                       (22.2)                  81   2,4-Difluoro                                                                           Neophyl                                                                              2 O            Viscous liquid   1.5821                                                                             23.1                                                                           (23.4)                  82   2,4-Difluoro                                                                           Neophyl                                                                              1 OAc          Viscous liquid   1.5598                                                                             21.3                                                                           (21.3)                  83   2,4-Difluoro                                                                           Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Viscous liquid   1.6156                                                                             19.1                                                                           (19.2)                  84   2,4-Difluoro                                                                           Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    131-134° C.                                                                         20.9                                                                           (21.0)                  85   3,4-Difluoro                                                                           Neophyl                                                                              1 F            Liquid           1.5793                                                                             23.2                                                                           (22.9)                  86   3,4-Difluoro                                                                           Neophyl                                                                              1 Cl           Liquid           1.5745                                                                             22.1                                                                               96.9                                                                       (22.2)                  87   3,4-Difluoro                                                                           Neophyl                                                                              2 O            Viscous liquid   1.5820                                                                             23.3                                                                           (23.4)                  88   3,4-Difluoro                                                                           Neophyl                                                                              1 OAc          Solid    33-35° C.                                                                           21.3                                                                           (21.3)                  89   3,4-Difluoro                                                                           Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    92-94° C.                                                                           19.5                                                                           (19.2)                  90   3,4-Difluoro                                                                           Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    50-53° C.                                                                           20.8                                                                           (21.0)                  91   2,4,5-Trifluoro                                                                        Neophyl                                                                              1 F            Liquid           1.5644                                                                             22.0                                                                           (22.2)                  92   2,4,5-Trifluoro                                                                        Neophyl                                                                              1 Cl           Solid    65-67° C.                                                                           21.7                                                                               99.9                                                                       (21.5)                  93   2,4,5-Trifluoro                                                                        Neophyl                                                                              2 O            Viscous liquid   1.5729                                                                             22.4                                                                           (22.6)                  94   2,4,5-Trifluoro                                                                        Neophyl                                                                              1 OAc          Solid    59-61° C.                                                                           20.8                                                                           (20.6)                  95   2,4,5-Trifluoro                                                                        Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    81-83° C.                                                                           18.7                                                                           (18.7)                  96   2,4,5-Trifluoro                                                                        Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    125-130° C.                                                                         20.2                                                                           (20.3)                  97   o-Cl    Neophyl                                                                              1 F            Solid    72-74°                                                                              23.2                                                                           (23.0)                  98   o-Cl    Neophyl                                                                              1 Cl           Viscous liquid   1.5981                                                                             22.2                                                                           (22.3)                  99   o-Cl    Neophyl                                                                              2 O            Viscous liquid   1.6070                                                                             23.4                                                                           (23.5)                  100  o-Cl    Neophyl                                                                              1 OAc          Viscous liquid   1.5800                                                                             21.2                                                                           (21.4)                  101  o-Cl    Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    100-103° C.                                                                         19.1                                                                           (18.7)                  102  m-Cl    Neophyl                                                                              1 F            Solid    58-62° C.                                                                           23.1                                                                           (23.0)                  103  m-Cl    Neophyl                                                                              1 Cl           Solid    41-43° C.                                                                           22.3                                                                               96.3                                                                       (22.3)                  104  m-Cl    Neophyl                                                                              2 O            Viscous liquid   1.6048                                                                             23.6                                                                           (23.5)                  105  m-Cl    Neophyl                                                                              1 OAc          Viscous liquid   1.5801                                                                             21.5                                                                           (21.4)                  106  m-Cl    Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Viscous liquid   1.6326                                                                             19.0                                                                           (19.2)                  107  m-Cl    Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    165-169° C.                                                                         21.1                                                                           (21.0)                  108  p-Cl    Neophyl                                                                              1 F            Solid    104-105° C.                                                                         23.0                                                                           (23.0)                  109  p-Cl    Neophyl                                                                              1 Cl           Solid    70-72° C.                                                                           22.6                                                                               99.0                                                                       (22.3)                  110  p-Cl    Neophyl                                                                              2 O            Viscous liquid   1.6045                                                                             23.4                                                                           (23.5)                  111  p-Cl    Neophyl                                                                              1 OAc          Viscous liquid   1.5808                                                                             21.5                                                                           (21.4)                  112  p-Cl    Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    89-92° C.                                                                           19.3                                                                           (19.2)                  113  p-Cl    Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    70-73° C.                                                                           20.8                                                                           (21.0)                  114  p-Me    Neophyl                                                                              1 F            Viscous liquid   1.5925                                                                             24.2                                                                           (24.0)                  115  p-Me    Neophyl                                                                              1 Cl           Solid    34.5-35.5° C.                                                                       23.5                                                                               96.7                                                                       (23.2)                  116  p-Me    Neophyl                                                                              2 O            Viscous liquid   1.6013                                                                             24.4                                                                           (24.5)                  117  p-Me    Neophyl                                                                              1 OAc          Viscous liquid   1:5780                                                                             22.4                                                                           (22.2)                  118  p-Me    Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    126-128° C.                                                                         20.1                                                                           (19.9)                  119  p-Me    Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    103-108° C.                                                                         21.5                                                                           (21.8)                  120  m-Me    Neophyl                                                                              1 F            Solid    58-59° C.                                                                           24.0                                                                           (24.0)                  121  m-Me    Neophyl                                                                              1 Cl           Viscous liquid   1.5893                                                                             23.5                                                                               98.2                                                                       (23.2)                  122  m-Me    Neophyl                                                                              2 O            Viscous liquid   1.5969                                                                             24.8                                                                           (24.5)                  123  m-Me    Neophyl                                                                              1 OAc          Viscous liquid   1.5748                                                                             22.5                                                                           (22.2)                  124  m-Me    Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    51-54° C.                                                                           20.1                                                                           (19.9)                  125  m-Me    Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    130-135° C.                                                                         21.5                                                                           (21.8)                  126  p-Me    Neophyl                                                                              1 F            Solid    95-98° C.                                                                           24.1                                                                           (24.0)                  127  p-Me    Neophyl                                                                              1 Cl           Solid    51-53° C.                                                                           23.3                                                                               99.3                                                                       (23.2)                  128  p-Me    Neophyl                                                                              2 O            Viscous liquid   1.5982                                                                             24.7                                                                           (24.5)                  129  p-Me    Neophyl                                                                              1 OAc          Viscous liquid   1.5755                                                                             22.4                                                                           (22.2)                  130  p-Me    Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    92-94° C.                                                                           20.2                                                                           (19.9)                  131  p-Me    Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    146-148° C.                                                                         21.5                                                                           (21.8)                  132  o-OMe   Neophyl                                                                              1 F            Viscous liquid   1.5885                                                                             23.0                                                                           (23.2)                  133  o-OMe   Neophyl                                                                              1 Cl           Solid    69-72° C.                                                                           22.7                                                                               99.5                                                                       (22.5)                  134  o-OMe   Neophyl                                                                              2 O            Viscous liquid   1.6013                                                                             24.1                                                                           (23.7)                  135  o-OMe   Neophyl                                                                              1 OAc          Viscous liquid                                                                          93-96°                                                                          1.5756                                                                             21.8                                                                           (21.5)                  136  o-OMe   Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Solid    93-96° C.                                                                           19.6                                                                           (19.4)                  137  o-OMe   Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    107-113° C.                                                                         21.3                                                                           (21.2)                  138  p-OMe   Neophyl                                                                              1 F            Viscous liquid   1.5943                                                                             23.4                                                                           (23.2)                  139  p-OMe   Neophyl                                                                              1 Cl           Viscous liquid   1.5918                                                                             22.7                                                                               96.2                                                                       (22.5)                  140  p-OMe   Neophyl                                                                              2 O            Viscous liquid   1.6004                                                                             23.5                                                                           (23.7)                  141  p-OMe   Neophyl                                                                              1 OAc          Viscous liquid   1.5777                                                                             21.9                                                                           (21.5)                  142  p-OMe   Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Viscous liquid   1.6281                                                                             19.0                                                                           (19.4)                  143  p-OMe   Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    134-140° C.                                                                         21.4                                                                           (21.2)                  144  H       Neophyl                                                                              1 F            Solid    37-40° C.                                                                           24.9                                                                           (24.7)                  145  H       Neophyl                                                                              1 Cl           Viscous liquid   1.5937                                                                             24.3                                                                               97.1                                                                       (23.9)                  146  H       Neophyl                                                                              2 O            Viscous liquid   1.6021                                                                             24.8                                                                           (25.2)                  147  H       Neophyl                                                                              1 OAc          Viscous liquid   1.5769                                                                             23.1                                                                           (22.8)                  148  H       Neophyl                                                                              1 SSCN(Me).sub.2                                                                              Viscous liquid   1.6343                                                                             20.6                                                                           (20.4)                  149  H       Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                          Solid    130-135° C.                                                                         22.5                                                                           (22.4)                  150  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 F            Solid    98-102° C.                                                                          25.9                                                                           (26.4)                  151  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 Cl           Solid    51-52° C.                                                                           25.4                                                                               98.6                                                                       (25.5)                  152  o-CF.sub.3                                                                             Cyclohexyl                                                                           2 O            Solid    125-128° C.                                                                         26.2                                                                           (27.1)                  153  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 OAc          Liquid           1.5250                                                                             23.8                                                                           (24.3)                  154  o-CF.sub.3                                                                             Cyclohexyl                                                                           1                                                                                 ##STR19##   Liquid           1.5111                                                                             21.8                                                                           (22.3)                  155  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 SCH.sub.2 COOn-Bu                                                                           Liquid           1.5400                      156  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 SCH.sub.2 COOn-Oct                                                                          Liquid           1.5312                      157  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Solid    154-156° C.                                                                         21.7                                                                           (21.7)                  158  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                          Solid    176-180° C.                                                                         23.5                                                                           (23.8)                  159  m-CF.sub.3                                                                             Cyclohexyl                                                                           2 O            Solid    84-86° C.                                                                           26.9                                                                           (27.1)                  160  m-CF.sub.3                                                                             Cyclohexyl                                                                           1 OAc          Solid    59-61° C.                                                                           25.0                                                                           (24.3)                  161  m-CF.sub.3                                                                             Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Solid    124-126° C.                                                                         21.6                                                                           (21.6)                  162  m-CF.sub.3                                                                             Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                          Solid    191-184° C.                                                                         22.9                                                                           (23.8)                  163  p-CF.sub.3                                                                             Cyclohexyl                                                                           1 F            Solid    240° C.                                                                             26.4                                                                               99.0                                                           (decomp.)   (26.4)                  164  p-CF.sub.3                                                                             Cyclohexyl                                                                           1 Cl           Solid    74-75° C.                                                                           25.8                                                                           (25.5)                  165  p-CF.sub.3                                                                             Cyclohexyl                                                                           2 O            Solid    86-89° C.                                                                           26.8                                                                           (27.1)                  166  p-CF.sub.3                                                                             Cyclohexyl                                                                           1 OAc          Solid    68-71° C.                                                                           23.9                                                                           (24.3)                  167  p-CF.sub.3                                                                             Cyclohexyl                                                                           1 SCH.sub.2 COOn-Bu                                                                           Liquid           1.5337                                                                             20.4                                                                           (20.6)                  168  p-CF.sub.3                                                                             Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Solid    85-87° C.                                                                           21.7                                                                           (21.6)                  169  p-CF.sub.3                                                                             Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                          Solid    215-225° C.                                                                         23.4                                                                           (23.8)                  170  m-F     Cyclohexyl                                                                           1 F            Solid    225° C.                                                                             29.6                                                               (decomp.)   (29.7)                  171  m-F     Cyclohexyl                                                                           1 Cl           Solid    52-53° C.                                                                           28.7                                                                           (28.6)                  172  m-F     Cyclohexyl                                                                           2 O            Solid    44-46° C.                                                                           31.0                                                                           (30.6)                  173  m-F     Cyclohexyl                                                                           1 OAc          Solid    52-54° C.                                                                           27.1                                                                           (27.0)                  174  m-F     Cyclohexyl                                                                           1 SCH.sub.2 COOn-Bu                                                                           Liquid           1.5555                                                                             22.9                                                                           (22.5)                  175  m-F     Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Solid    110-112° C.                                                                         24.0                                                                           (23.7)                  176  m-F     Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                          Solid    208° C.                                                                             26.7                                                               (decomp.)   (26.5)                  177  o-CF.sub.3                                                                             Neophyl                                                                              1 SSCN(Et).sub.2                                                                              Liquid           1.5931                                                                             17.2                                                                           (17.5)                  178  o-CF.sub.3                                                                             Neophyl                                                                              1 o-t-Butylphenoxy                                                                            Solid    75-76° C.                                                                           17.5                                                                           (17.5)                  179  o-CF.sub.3                                                                             Neophyl                                                                              1 2,6-Diisopropylphenoxy                                                                      Liquid           1.5619                                                                             16.7                                                                           (16.8)                  180  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 SSCN(Et).sub.2                                                                              Solid    105-107° C.                                                                         20.6                                                                           (20.5)                  181  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 o-t-Butylphenoxy                                                                            Liquid           1.5519                                                                             19.9                                                                           (20.5)                  182  o-CF.sub.3                                                                             Cyclohexyl                                                                           1 2,6-Diisopropylphenoxy                                                                      Solid    53-57° C.                                                                           19.3                                                                           (19.5)                  183  p-Cl    Cyclohexyl                                                                           1 F            Solid    256-258° C.                                                                         28.2                                                                           (28.6)                  184  p-Cl    Cyclohexyl                                                                           1 Cl           Solid    49-50° C.                                                                           27.1                                                                           (27.5)                  185  p-Cl    Cyclohexyl                                                                           2 O            Solid    111-113° C.                                                                         29.4                                                                           (29.3)                  186  p-Cl    Cyclohexyl                                                                           1 OAc          Solid    97-99° C.                                                                           26.4                                                                           (26.1)                  187  p-Cl    Cyclohexyl                                                                           1 SCH.sub.2 COOn-Bu                                                                           Liquid           1.5645                                                                             21.9                                                                           (21.8)                  188  p-Cl    Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Solid    70-73° C.                                                                           22.5                                                                           (23.0)                  189  p-Cl    Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                          Solid    217-223° C.                                                                         25.5                                                                           (25.5)                  190  3,4-Dichloro                                                                           Cyclohexyl                                                                           1 F            Solid    193° C.                                                                             26.0                                                               (decomp.)   (26.4)                  191  3,4-Dichloro                                                                           Cyclohexyl                                                                           1 Cl           Liquid           1.5903                                                                             25.1                                                                               97.2                                                                       (25.4)                  192  3,4-Dichloro                                                                           Cyclohexyl                                                                           2 O            Solid    129-130° C.                                                                         27.4                                                                           (27.0)                  193  3,4-Dichloro                                                                           Cyclohexyl                                                                           1 OAc          Solid     99-101° C.                                                                         24.4                                                                           (24.2)                  194  3,4-Dichloro                                                                           Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Solid    138-140° C.                                                                         21.5                                                                           (21.5)                  195  3,4-Dichloro                                                                           Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                          Solid    207-213° C.                                                                         24.0                                                                           (23.8)                  196  p-Me    Cyclohexyl                                                                           1 F            Solid    245-247° C.                                                                         29.7                                                                           (30.0)                  197  p-Me    Cyclohexyl                                                                           1 Cl           Liquid           1.5705                                                                             28.6                                                                           (28.8)                  198  p-Me    Cyclohexyl                                                                           2 O            Solid    71-73° C.                                                                           31.0                                                                           (30.9)                  199  p-Me    Cyclohexyl                                                                           1 OAc          Solid    83-85° C.                                                                           27.6                                                                           (27.3)                  200  p-Me    Cyclohexyl                                                                           1 SCH.sub.2 COOn-Bu                                                                           Liquid           1.5605                                                                             22.9                                                                           (22.7)                  201  p-Me    Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Solid    92-94° C.                                                                           23.8                                                                           (23.9)                  202  p-Me    Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                          Solid    205-210° C.                                                                         26.5                                                                           (26.7)                  203  p-Methoxy                                                                              Cyclohexyl                                                                           1 F            Solid    234-236° C.                                                                         29.4                                                                           (28.9)                  204  p-Methoxy                                                                              Cyclohexyl                                                                           1 Cl           Liquid           1.5749                                                                             27.6                                                                               96.9                                                                       (27.8)                  205  p-Methoxy                                                                              Cyclohexyl                                                                           2 O            Solid    65-69° C.                                                                           29.6                                                                           (29.7)                  206  p-Methoxy                                                                              Cyclohexyl                                                                           1 OAc          Solid    82-84° C.                                                                           26.7                                                                           (26.3)                  207  p-Methoxy                                                                              Cyclohexyl                                                                           1 SCH.sub.2 COOn-Bu                                                                           Liquid           1.5630                                                                             22.5                                                                           (22.0)                  208  p-Methoxy                                                                              Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                              Solid    78-80° C.                                                                           23.1                                                                           (23.2)                  209  p-Methoxy                                                                              Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                          Solid    202-207° C.                                                                         25.4                                                                           (25.8)                  __________________________________________________________________________

                                      TABLE 1-2                                    __________________________________________________________________________      ##STR20##                                                                                                         Physical property                                                                                Tin  GLC                 Compound                                   m.p. or    content                                                                             purity              No.   R*           R.sup.1                                                                              m X        Appearance                                                                            b.p.   n.sup.30                                                                           (%)  (%)                 __________________________________________________________________________     210   2-Thienyl    Neophyl                                                                              1 Cl        Viscous liquid                                                                              1.5987                                                                             23.5                                                                           (23.6)                   211   2-Thienyl    Neophyl                                                                              2 O        Solid  90-99° C.                                                                          24.7                                                                           (24.9)                   212   2-Thienyl    Neophyl                                                                              1 OAc      Viscous liquid                                                                               1.5798                                                                             22.5                                                                           (22.6)                   213   2-Thienyl    Neophyl                                                                              1 SSCN(Me).sub.2                                                                          Solid  77-79° C.                                                                          20.4                                                                           (20.2)                   214   2-Thienyl    Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                      Solid  147-157° C.                                                                        21.8                                                                           (22.1)                   215   3-Thienyl    Neophyl                                                                              1 F        Solid  85-90° C.                                                                          24.7                                                                           (24.4)                   216   3-Thienyl    Neophyl                                                                              1 Cl       Viscous liquid                                                                               1.5988                                                                             23.9 97.8                                                                      (23.6)                   217   3-Thienyl    Neophyl                                                                              2 O        Solid  78-81° C.                                                                          25.0                                                                           (24.9)                   218   3-Thienyl    Neophyl                                                                              1 OAc      Solid  46-48° C.                                                                          22.7                                                                           (22.5)                   219   3-Thienyl    Neophyl                                                                              1 SSCN(Me).sub.2                                                                          Solid  87-89° C.                                                                          20.6                                                                           (20.2)                   220   3-Thienyl    Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                      Solid  140-144° C.                                                                        21.9                                                                           (22.1)                   221   Trimethylsilylmethyl                                                                        Neophyl                                                                              1 F        Liquid        1.5412                       222   Trimethylsilylmethyl                                                                        Neophyl                                                                              1 Cl       Solid  42.5-43.5° C.                                                                           99.0                223   Trimethylsilymethyl                                                                         Neophyl                                                                              2 O        Solid  90.5-91.0° C.                224   Trimethylsilylmethyl                                                                        Neophyl                                                                              1 OAc      Liquid        1.5372                       225   Trimethylsilylmethyl                                                                        Neophyl                                                                              1 SSCN(Me).sub.2                                                                          Solid  62-63° C.                    226   Trimethylsilylmethyl                                                                        Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                      Solid  78-85°  C.                   227   Dimethylphenylsilylmethyl                                                                   Neophyl                                                                              1 Cl       Solid  30° C.   99.0                228   Dimethylphenylsilylmethyl                                                                   Neophyl                                                                              2 O        Solid  87-89° C.                    229   Dimethylphenylsilylmethyl                                                                   Neophyl                                                                              1 OAc      Liquid        1.5617                       230   Dimethylphenylsilylmethyl                                                                   Neophyl                                                                              1 SSCN(Me).sub.2                                                                          Liquid        1.6141                       231   Trimethylsilylmethyl                                                                        Cyclohexyl                                                                           1 F        Solid  167-170° C.                  232   Trimethylsilylmethyl                                                                        Cyclohexyl                                                                           1 Cl       Solid  74° C.   99.0                233   Trimethylsilylmethyl                                                                        Cyclohexyl                                                                           2 O        Solid  151-153° C.                  234   Trimethylsilylmethyl                                                                        Cyclohexyl                                                                           1 OAc      Solid  52-53° C.                    235   Trimethylsilylmethyl                                                                        Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                          Solid  101-102° C.                  236   Trimethylsilylmethyl                                                                        Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                      Solid  197-201° C.                                                             (decomp.)                           237   Trimethylsilylmethyl                                                                        Cyclohexyl                                                                           1                                                                                 ##STR21##                                                                              Solid  130-132° C.                  238   Neopentyl    Neophyl                                                                              1 Cl       Solid  65-66° C.                                                                          23.6 99.9                                                                      (24.1)                   239   Neopentyl    Neophyl                                                                              2 O        Solid  100-101° C.                                                                        25.7                                                                           (25.6)                   240   Neopentyl    Cyclohexyl                                                                           1 Cl       Solid  106-107° C.                                                                        29.5                                                                           (30.3)                   241   Neopentyl    Cyclohexyl                                                                           2 O        Solid  202-203° C.                                                                        32.5                                                                           (32.6)                   242   Dimethylphenylsilylmethyl                                                                   Neophyl                                                                              1 F        Solid  47-48° C.                    243   Dimethylphenylsilylmethyl                                                                   Neophyl                                                                              1 1,2,4-Triazol-1-yl                                                                      Solid  66-71° C.                    244   Dimethylphenylsilylmethyl                                                                   Neophyl                                                                              1                                                                                 ##STR22##                                                                              Liquid        1.5484                       245   Dimethylphenylsilylmethyl                                                                   Cyclohexyl                                                                           1 F        Solid  107-110° C.                  246   Dimethylphenylsilylmethyl                                                                   Cyclohexyl                                                                           1 Cl       Liquid        1.5593                       247   Dimethylphenylsilylmethyl                                                                   Cyclohexyl                                                                           2 O        Solid  48-51° C.                    248   Dimethylphenylsilylmethyl                                                                   Cyclohexyl                                                                           1 OAc      Liquid        1.5421                       249   Dimethylphenylsilylmethyl                                                                   Cyclohexyl                                                                           1 SSCN(Me).sub.2                                                                          Liquid        1.6054                       250   Dimethylphenylsilylmethyl                                                                   Cyclohexyl                                                                           1 1,2,4-Triazol-1-yl                                                                      Solid  118-124° C.                  251   Dimethylphenylsilylmethyl                                                                   Cyclohexyl                                                                           1                                                                                 ##STR23##                                                                              Solid  125-126° C.                  __________________________________________________________________________

Various compounds to be employed in accordance with the present invention were formulated as wettable powders, emulsifiable concentrates, fine dusts, etc., as shown below.

    ______________________________________                                         Ingredient        Part by weight                                               ______________________________________                                         Formulation 1 Wettable powder                                                  Compound No. 28   50.0                                                         Clay              40.5                                                         White carbon      5.0                                                          Polyoxyalkylenealkyl-                                                                            3.0                                                          allylethersulfate                                                              Alkylbenzensulfonate                                                                             1.5                                                          Formulation 2 Emulsifiable concentrate                                         Compound No. 25   25.0                                                         Alkylallylsulfonate                                                                              3.0                                                          Polyoxyalkylenealkylallyl                                                                        10.0                                                         ether                                                                          Xylene            42.0                                                         Dimethylformamide 20.0                                                         ______________________________________                                    

Compound No. 25, alkylallylsulfonate and polyoxyalkylenealkylallyl ether are uniformly dissolved in xylene and dimethylformamide to obtain emulsifiable concentrate. The preparation is diluted with water when use.

    ______________________________________                                         Formulation 3 Fine dust                                                        ______________________________________                                         Compound No. 33    15.0                                                        White carbon       20.0                                                        Isopropylazidophosphate                                                                           0.3                                                         Fine clay          64.7                                                        ______________________________________                                    

The above ingredients are mixed and ground. The mixture is finely ground by Jetmizer grinder to obtain fine dust. The preparation is used as it is.

    ______________________________________                                         Formulation 4 Dust                                                             ______________________________________                                         Compound No. 49  5.0                                                           Clay             91.7                                                          White carbon     3.0                                                           Tall oil         0.3                                                           ______________________________________                                    

The above ingredients are mixed and ground to obtain dust preparation. The dust is used as it is.

Experiment 1 Sample

Compounds of the invention to be tested are dissolved in a minimum of DMF. Distilled water containing Tween 20 at the concentration of 100 ppm is thereto added to prepare a series of samples of the desired concentrations.

Test Procedure

A. Suppression of Spodoptera litura (common cutworm) larvae

Cabbage leaves (5×5 cm) were immersed in the sample solution as prepared above and air dried. Two leaves were placed in a petri dish (9 cm diameter) and 10 third-instar larvae of Spodoptera litura were placed in the dish. The dish was held at 25° C. and the mortality of the larvae was measured after 48 hours.

C. Suppression of Plutella xylostella (diamond backmoth) larvae

Cabbage leaf (7×7 cm) was immersed in the sample solution and air dried. The leaf was placed in a petri dish (9 cm diameter) and 10 third-instar larvae of Plutella xylostella were placed in the dish. The dish was held at 25° C. and the mortality of the larvae was measured after 48 hours.

D. Suppression of Adoxophyes sp. larvae

Whole tea leaves were immersed in the sample solution and air dried. Three leaves were placed in a polyethylene petri dish (6 cm diameter, 4 cm depth) and 10 forth-instar larvae of Adoxophyes sp. were placed in the dish. The dish was held at 25° C. and the mortality of the larvae was measured after 48 hours.

E. Suppression of Nephotettix cincticeps (green rice leaf hopper) (sensitive)

Six or seven rice seedlings of 1.5 to 2 plant age in leaf number were bundled and the roots were wrapped in sponge.The seedlings were placed in a polyethylene cup (diameter 6 cm, depth 4 cm) and the cup is placed in a rotary application tower, whereby the leaves and sheaths of the seedlings were sprayed with 2 ml of the sample solution and air dried. The treated seedlings were covered with a transparent plastic cylinder and ten female larvae were placed in the cylinder. The atmosphere in the cylinder was ketp at 25° C., and the mortality after 48 hours was measured.

I. and J. Suppression of Myzus persicae (green peach aphid) larvae (I: sensitive, J: resistant)

A polyethylene cup (diameter 6 cm, depth 4 cm) was filled with 0.3% agar gel and a piece of Chinese cabbage leaf (3×3 cm) was placed on the gel. An apterous adult of Myzus persicae was placed on the cabbage and allowed to egg-deposit while keeping the surrounding atmosphere at 25° C. for 24 hours. After removing the adult, 2 ml of the sample was sprayed on the leaf under a rotary application tower. The test system was kept at 25° C. for 48 hours and the mortality of born larvae was measured.

M. Suppression of Tetranychus cinnabrinus (carmine spider mite)

A polyethylene cup (diameter 6 cm, depth 4 cm) was filled with 0.3% agar gel and a piece of bush bean leaf (diameter 2 cm) was placed on the gel. About twelve adults of Tetranychus cinnabrinus were placed on the leaf. After 24 hours at 25° C., dead and feeble adults were removed and 2 ml of the sample solution was sprayed on the leaf and audlts under a rotary application tower. Following such treatment the test system was kept at 25° C. and the mortality was measured after 48 hours.

O. Suppression of Tetranychus urticae (Two-spotted spider mite)

The same test procedure as above was repeated on Tetranychus urticae.

X. Suppression of Tetranychus cinnabrinus larvae

A polyethylene cup (diameter 6 cm, depth 4 cm) was filled with 0.3% agar gel and a piece of bush bean leaf (diameter 2 cm) was placed on the gel. Seven adults of Tetranychus cinnabrinus were placed on the leaf and allowed to egg-deposit while keeping the surrounding atmosphere at 25° C. for 24 hours. After removing the adult, 2 ml of the sample was sprayed on the leaf under a rotary application tower. The test system was kept at 25° C. for 7 days and the mortality of born larvae was measured.

Y. Suppression of Tetranychus urticae larvae

The same test procedure as above was repeated on Tetranychus urticae larvae.

N. Suppression of Tetranychus cinnabrinus eggs

P. Suppression of Tetranychus urticae eggs

The test procedure as described in X and Y were repeated on Tetranychus cinnabrinus and urticae eggs. The test system was kept at 25° C. for 7 days and the mortality of eggs was measured by counting the number of eggs which did not hatch.

T. Suppression of Henosepilachna vigintioctopunctata (twenty-eight-spotted beetle) adults

Japanese eggplant leaf (6×6 cm) was immersed in the sample solution and air dired. The leaf was placed in a petri dish (9 cm diameter) and 5 adults of Henosepilachna vigintioctopunctata were placed in the dish. The dish was held at 25° C. and the mortality was measured after 48 hours.

R. Suppression of Periplaneta americana (American cockroach) larvae

A filter paper soaked with the sample solution was placed in a petri dish (diameter 9 cm). Five Periplaneta americana larvae within 7 days after hatching were placed in the dish hold at 25° C. and the mortality after 48 hours was measured.

W. Suppression of Callosobruchus chinensis (adzuki bean weevil)

Ten Callosobruchus chinensis adults within 24 hours after hatching were placed in a screw cylinder (diameter 1.8 cm, height 5 cm) with stainless nets at the up-and-down openings. The cylinder was submerged in the sample solution, and the adults exposed to the solution were air dried. The mortality was measured after 48 hours at 25° C.

K. Suppression of Panonychus citri (citrus red mite)

The same test procedure as M and O was repeated on Panonychus citri except that lemon leaf, rather than bush bean leaf, was employed.

Q. Suppression of Tetranychus kanzawai (kanzawa spider mite) (resistant adults)

The same test procedure as M and O was repreated on resistant adults of Teranychus kanzawai.

Test Results

Table 2 below shows the mortality (%) of various pests exposed to the indicated compounds (I) at several concentrations, wherein the following codes are employed for pests.

A: Spodoptera litura (larvae)

C: Plutella xylostella (larvae)

D: Adoxophyes sp. (larvae)

E: Nephotettix cincticeps (sensitive adults)

I: Myzus persicae (sensitive larvae)

J: Myzus persicae (resistant larvae)

K: Panonychus citri (adults)

L: Panonychus citri (eggs)

M: Tetranychus cinnabrinus (adults)

N: Tetranychus cinnabrinus (eggs)

O: Tetranychus urticae (adults)

P: Tetranychus urticae (eggs)

Q: Tetranychus kanzawai (resistant adults)

R: Periplaneta americana (larvae)

T: Henosepilachna vigintioctopunctata (adults)

W: Callosobruchus chinensis (adults)

X: Tetranychus cinnabrinus (eggs-larvae)

Y: Tetranychus urticae (eggs-larvae)

Table 2 also lists the test results on commercially available Osadan® and Plictran® employed as a control.

Resistant adults of Tetranychus kanzawai used in Test Q were those which acquired resistance against Osadan® and Plictran® and were gathered at Yaguchihara and Okadahara, Shizuoka, Japan. Test results on the adults from Yaguchihara and Okadahara are shown on the left and right, respectively, of column "Q" in Table 2.

                                      TABLE 2                                      __________________________________________________________________________         Con-                                                                           cen-                                                                       Com-                                                                               tra-                                                                       pound                                                                              tion                                                                       No. (ppm)                                                                              A  C  D E  G H                                                                               I  J  K  L M  N  O  P  Q  R  T  W      X                                                                       Y                        __________________________________________________________________________     Osadan                                                                             1000                         100                                                                               93       47 52       100                       250                          100   95    37 36           100                                                                     100                          63                           90          27 16           80                Plic-                                                                              1000                                                                               100                      100         51 69           100               tran                                                                               250 100                      100   100   23 36           100                                                                     100                          63  100                      100   93    10 24           40                                                                      50                           15                           88           1  3                             1   1000                         100                                                                               70       97              100                   250                                100     90            90                    63                      97         100                                         16                                 77                                      2   1000                                                                               100                      100                                               250 100                      100   100                                         63  70                       100   97                                      3   1000                         100                         100                   250                                100                   100                   63                      87         100                   70                    16                                 79                                      4   1000              100        100                                                                               70                       100                   250                                100                                                                               97   70            100                   63                      91         100                   80                    16                                 76                                      5   1000                         100                         100                   250                                100                                                                               71   76            100                   63                      97         100                   80                    16                      89         80                                      6   1000                         100                         100                   250                                100                   100                   63                      90         100                   80                    16                      86         72                                      7   1000              100        100                                                                               81       96              100                   250               92 100           100   80 89           90                    63                      95         100     74                                  16                                 78                                      8   1000              100        100                                                                               95       100             100                   250               95 100           100                                                                               83 79 93           100                   63                      94         100                                     9   1000                         100         100             100                   250                          100                                                                               70 100                                                                               79 85 96           100                                                                     100                          63                      97   100   100     84            95                                                                      90                           16                           74       88                                   10  1000                         100         96              100                   250                                100                                                                               95   96            100                   63                      84         100                   70                    16                                 93                                      11  1000                                                                               100     72    100        100                                                                               90          80 100                                                                               100    100                   250 100                                                                               95         100                                                                               92      100                                                                               75 100                   100                                                                     100                          63     70         87 81      100   95                                      12  1000   100                      93 100                   100                   250 90 90                                                95                                                                      80                           63                                                                         16  1000              100        100                                                                               87       100             100                   250               86 100           100                                                                               88 76 93           100                   63                      100        100     79                                  16                      74         92                                      17  1000                         100         97              100                   250                          100                                                                               80 86 81 89       100    100                   63                      97   100   100                   100                                                                     98                           16                           73    75                    85                18  1000                         100                         100                   250                                100                                                                               87 78 92           100                   63                      94         100                                                                               70   70            100                   16                                 91                    80                19  1000                                                                               100     100   100        100                                                                               95          80 100                                                                               100    100                   250 80 80         84 100     100                                                                               92 100                   100                                                                     100                          63                81 86      100   98                                          16                           91                                            20  1000                                                                               70            100        100                                                                               100                      100                   250                          97    97                    70                                                                      80                           63                           80                                            23  1000                                                                               100                      94                          98                    250 90 100                                                                     63                                                                         25  1000              100        100                                                                               85       100                                                                               100          100                   250               94 100           100   86 89           100                   63                      97         97                    80                21  1000                                                                               100           100        100                                                                               83          80           100                   250 80 100        100                                                                               93      100   100                                         63                           100   100                                         16                                                                         24  1000                                                                               75            100        100                                                                               100         80           100                   250               90 100     100   100                   70                                                                      100                          63                   73      92    97                                      26  1000                         100         100             100                   250                          100   100                                                                               78 83 93           100                                                                     100                          63                      97   91    97                    100                                                                     95                           16                                                       85                                                                      70                       27  1000              100        100                         100                   250                                100                                                                               88   97            100                   63                                 100                   95                    16                                 82                    70                28  1000              100        100                                                                               96          100                                                                               100                                                                               100    100                   250               100                                                                               100     100   100                                                                               71                 100                                                                     100                          63                95         100   100                                     29  1000                                                                               100           100        100                                                                               85          100          100                   250 75            100        100   100                                         63                77         97    100                                     30  1000                         100                                               250                                                                            63                                                                         31  1000                                                                               100                      93                          95                    250 95 85                                                                      63                                                                             16                                                                         32  1000                                                                               100           100        100               100       80                    250 80 80         83         100   94                                      33  1000              100        100         100             100                   250               93 100           100                                                                               70 86 92           100                   63                      92         100                                         16                      72         77                                      34  1000                         100         100             100                   250                          100                                                                               84 100   83 96           100                                                                     100                          63                      97   100   100     79            80                                                                      98                           16                      78         79                    80                35  1000                         100                         100                   250                                100                                                                               74                 100                   63                      94         100                   90                    16                                 93                                      36  1000                                                                               100     84    100        100                                                                               98          100                                                                               100                                                                               100    100                   250 70 75         100        100                                                                               85 100                   100                                                                     100                          63                74         100   100                                     37  1000                                                                               85            100        100                                                                               100                                            250               100                                                                               100     100                                                                               74 100                                                                               75                 100                                                                     100                          63                           93    88                                      38  1000                                                                               100           100        100                                                                               95                                             250 95 75         100                                                                               100     100   100                   100                   63                           100   100                   100               39  1000                         84 92                       100                   250                                                      100               40  1000                                                                               100           100        100   91                    100                                                                     100                          250                          87                          100                                                                     90                       41  1000              100        100                                                                               73       85              100                   250                                100     73            90                    63                      97         92                                      42  1000                         100                                                                               72       100             100                   250                          100                                                                               84 100     96            100                                                                     100                          63                      97   100   100     71            70                                                                      98                           16                      91   84    70                                      43  1000                         100                         100                   250                                100                                                                               92   89            100                   63                      90         97 71                 80                    16                                 84                                      44  1000                                                                               100           100        100                                                                               100                                            250 70            100                                                                               90      100                                                                               92 100                   100                                                                     100                          63                           80    94                                      45  1000                                                                               100           100        100                                                                               100                                            250    80         84 100     100                                                                               85 100                                         63                           93    70                                      46  1000                                                                               100           100        100                                                                               82          100          100                   250               100                                                                               100     100   100                   80                                                                      100                          63                100                                                                               69      97    100                                     47  1000              85         100                  90                           250                          100   93                                      48  1000                                                                               100                      100                         100                   250                          85    88                    100                                                                     100                          63                         90                                                                               71                          95                49  1000                         100                         100                   250                          100                                                                               84 100                   100                                                                     100                          63                      91   94    100                   70                                                                      70                       50  1000                                                     100                   250                                100                                                                               82                 95                    63                      82         97                                          16                                 82                                      51  1000                                                                               100           100        100                                                                               75          100          100                   250 85 75         100                                                                               100     100   100                                         63  70                       100   97                                      52  1000                                                                               100           100        100                                                                               100                                            250 80 80            75      100   100                   100                                                                     100                          63                           94    89                                      54  1000                         100                                               250                          100   100                                         63                           97    92                                      59  1000                                                                           250                                100                   100                   63                                 100                                     60  1000                                                                           250               75               100                   100                   63                                 100                                     61  1000                                                                           250                                100                   100                   63                                 97                                      62  1000                                                                           250                                89                    100                   63                                                                         63  1000                                                                           250                                97                    100                   63                                 100                                     64  1000                                                                           250                                                                            63                                 100                   90                    16                                 92                    80                65  1000                                                                           250                                                                            63                                 100                   70                66  1000                                                                           250               72               100                   90                    63                                 100                                     67  1000                                                                           250                                83                    90                68  1000                                                                           250               90               100                   100                   63                                 100                                         16                                 71                                      69  1000                                                                           250                                100                   100                   63                                 94                                      70  1000                                                                           250                                100                   100                   63                                 81                                      71  1000                                                                           250                                100                   100                   63                                 97                                      72  1000                                                                           250                                100                   100                   63                                 84                                      73  1000                                                                           250                                100                   100                   63                                 82                                      74  1000                                                                           250                                100                   100                   63                                 88                                      75  1000                                                                           250                                100                   100                   63                                 93                                      76  1000                                                                           250                                100                   100                   63                                 94                                      77  1000                                                                           250                                100                   100               78  1000                                                                           250                                100                   100                   63                                 79                                      79  1000                                                                           250                          100   100                                                                               100                98                    63                           79    97 95                                   80  1000                                                                           250                          100   100                                                                               100                98                    63                           83 70 89 70                                   81  1000                                                                           250                          100   100                                                                               100                100                   63                           87 80 100                                     82  1000                                                                           250                          100   100                                                                               100                100                   63                           90    92 80                                   83  1000                                                                           250                          96    100                                                                               100                100                   63                                 93 80                                   84  1000                                                                           250                          100   100                                                                               95                 100                   63                                 96                                      85  1000                                                                           250                          90                          100                   63                                 100                                         16                                 90                                      86  1000                                                                           250                          100   100                                                                               100                100                   63                           84 70 84 70                                   87  1000                                                                           250                          97    94 95                 100                   63                           73    76 70                                   88  1000                                                                           250                          100   100                                                                               100                100                   63                           90       90                                   89  1000                                                                           250                          100   93 100                100                   63                           77       95                                       16                                    80                                   90  1000                                                                           250                          94    100                                                                               100                100                   63                                 80 80                                   91  1000                                                                           250                          97                          98                    63                           74                                            92  1000                                                                           250               83         100                                                                               82 97                    80                    63                           84    93                                          16                                 74                                      93  1000                                                                           250                                100                   100                   63                                 97                                      94  1000                                                                           250                                100                   100                   63                                 95                                      95  1000                                                                           250                                100                   100                   63                                 91                                      96  1000                                                                           250                                100                   100                   63                                 100                                     97  1000                                                                           250               74               100                   100                   63                                 100                                         16                                 72                                      98  1000                                                                           250               94               100                                                                               78                 100                   63                                 97                                      99  1000                                                                           250                                100                   100                   63                                 100                                     100 1000                                                                           250                                100                   100                   63                                 95                                      101 1000                                                                           250                                100                   70                    63                                 94                                      102 1000                                                                           250                                100                   100                   63                                 94                                      103 1000                                                                           250                                100                   100                   63                                 93                                      104 1000                                                                           250                                100                   100                   63                                 100                                     105 1000                                                                           250                                100                   100                   63                                 97                                      106 1000                                                                           250                                72                    100                   63                                 89                                      107 1000              86                                                           250                                                                            63                                 93                    90                108 1000                                                                           250                                100                   100                   63                                 96                                      109 1000                                                                           250                                100                   100                   63                                 100                                     110 1000                                                                           250                                100                   100                   63                                 100                                     111 1000                                                                           250                                                      100                   63                                 92                                      112 1000                                                                           250                                100                   100                   63                                 91                                      113 1000                                                                           250                                100                   100                   63                                 90                                      114 1000                                                                           250                                                                            63                                 94                    90                    16                                                       80                115 1000                                                                           250                                                                            63                                 98                    80                    16                                 79                                      116 1000                                                                           250                                                                            63                                 92                    98                117 1000                                                                           250                                                                            63                                 90                                      118 1000                                                                           250                                                                            63                                 93                    75                    16                                                       75                119 1000                                                                           250                                                                            63                                 100                   85                    16                                 88                                      120 1000                                                                           250                                                      100                   63                                 100                                         16                                 91                                      121 1000                                                                           250                                                                            63                                 98                    100                   16                                 78                    90                122 1000                                                                           250                                                      100                   63                                 100                                         16                                 95                                      123 1000                                                                           250                                                      100                   63                                 96                                      124 1000                                                                           250                                                                            63                                 91                    70                125 1000                                                                           250                                                                            63                                 97                    90                126 1000                                                                           250                                                                            63                                 100                   80                    16                                 70                                      127 1000              76                                                           250                                                                            63                                 96                    98                    16                                                       80                128 1000                                                                           250                                                                            63                                 100                   90                    16                                                       80                129 1000                                                                           250                                                                            63                                 94                    95                    16                                                       80                130 1000                                                                           250                                                                            63                                 92                    95                131 1000                                                                           250                                                                            63                                 98                    90                132 1000                                                                           250                                                      100                   63                                 97                                          16                                 81                                      133 1000                                                                           250                                                                            63                                 88                    80                134 1000                                                                           250                                                      100                   63                                 97                                      135 1000                                                                           250                                                      100                   63                                 97                                      136 1000                                                                           250                                                                            63                                 89                    80                137 1000                                                                           250                                                      92                    63                                 92                                      138 1000                                                                           250                                                      100                   63                                 82                                      139 1000                                                                           250                                                      100                   63                                 81                                      140 1000                                                                           250                                                      100                   63                                 81                                      141 1000                                                                           250                                                      100               142 1000                                                                           250                                                      100               143 1000                                                                           250                                                      100                   63                                 81                                      144 1000                                                                           250                                                      100                   63                                 93                                          16                                 76                                      145 1000                                                                           250                                                      100                   63                                 100                                     146 1000                                                                           250                                                      100                   63                                 96                                      147 1000                                                                           250                                                      100                   63                                 98                                      148 1000                                                                           250                                                      100                   63                                 97                                      149 1000                                                                           250               73                                     100                   63                                 91                                      150 1000                                                                               100           100        100                                                                               100                                            250 75 90         100                                                                               100     100   100                                         63                           100   100                                         16                           97    94                                      151 1000                                                                               100           100        100                                                                               100                                            250    70         100                                                                               100     100   100                                         63                91 93      100   100                                         16                           97    97                                      152 1000                                                                           250 80            100        100                                                                               82                       100                   63                           74                                            153 1000                                                                           250 90            100        100                                                                               100                                            63                           94 100                                                                               97                                          16                                 76                                      154 1000                                                                           250               100                 94                 100                   63                                 100                                         16                                 90                                      155 1000                                                                           250                                                                            63                                 100                   99                    16                                 96                                      156 1000                                                                           250                                                                            63                                 100                   100                   16                                 93                                      157 1000                                                                           250                          100   100                                                                               100                100                   63                           100                                                                               100                                                                               97 95                                   158 1000                                                                           250 45            100        100                                                                               91                       100               159 1000                                                                               100                      100                         100                   250                          100   100                                         63                           97    100                                         16                           81    96                                      160 1000                         100                         100                   250 90            100        94                                                63                                 97                                      161 1000                                                                               100                      100                         100                   250    70                    100   100                                         63                           97    100                                         16                           83    86                                      162 1000                                                                               100                      100                         100                   250 70                       100   100                                         63                           100   100                                         16                           73    81                                      163 1000                                                                           250                                                      80                164 1000                                                                           250                                                      100                   63                                 100                                         16                                 83                                      165 1000                                                                           250                                                      100                   63                                 100                                         16                                 71                                      166 1000                                                                           250                                                      100                   63                                 100                                     167 1000                                                                           250                                                      100                   63                                 96                                          16                                 87                                      168 1000                                                                           250               86                                     100                   63                                 100                                         16                                 82                                      169 1000                                                                           250                                                      100                   63                                 100                                         16                                 90                                      170 1000                                                                           250                                                      100                   63                                 90                                      171 1000                                                                               95            81                                                           250                                                      100                   63                                 97                                          16                                 72                                      172 1000                                                                           250 90                                                   97                    63                                 96                                      173 1000                                                                           250 80                                                   100                   63                                 100                                         16                                 94                                      174 1000                                                                           250               100                                    100                   63                                 100                                         16                                 72                                      175 1000                                                                           250               100                                    100                   63                                 91                                      176 1000                                                                           250 90                                                   100                   63                                 97                                          16                                 76                                      210 1000                                                                           250                                                      100                   63                                 85                                      211 1000                                                                           250                                                      95                    63                                 78                                      212 1000                                                                           250                                                      70                213 1000                                                                           250                                                      95                214 1000                                                                           250                                                      70                    63                                 77                                      216 1000                                                                           250                                                      100                   63                                 95                                          16                                 70                                      217 1000                                                                           250                                                      100                   63                                 95                                      218 1000                                                                           250                                                      100                   63                                 93                                      219 1000                                                                           250                                                      100                   63                                 84                                      220 1000                                                                           250                                                      100                   63                                 95                                      221 1000                                                                           250               85                  76                 100                   63                                 100                                         16                                 97                                      222 1000                                                                           250               100                                    80                    63                                 100                                         16                                 93                                      223 1000                                                                           250               92                  88                 100                   63                                 100                                         16                                 97                                      224 1000                                                                           250               100                                    100                   63                                 100                                         16                                 84                                      225 1000                                                                           250               83                                     100                   63                                 100                                         16                                 93                                      226 1000                                                                           250               86                  79                 100                   63                                 100                                         16                                 97                                      227 1000                                                                           250               100                                    100                   63                                 100                                         16                                 76                                      228 1000                                                                           250               100                                    100                   63                                 92                                      229 1000                                                                           250               100                                    100                   63                                 93                                      230 1000                                                                           250                                                      100                   63                                 100                                     231 1000                                                                           250 100           100                 100                                      63                                 100                                         16                                 93                                      232 1000                                                                           250 100           100                                    100                   63                                 100                                         16                                 96                                      233 1000                                                                           250 100                               98                 100                   63                                 100                                         16                                 96                                      234 1000                                                                           250 100                               100                                      63                                 100                                         16                                 96                                      235 1000                                                                           250 100                               92                 100                   63                                 100                                         16                                 96                                      236 1000                                                                           250 90            100                                    100                   63                                 100                                                                               91                                       16                                 86                                      237 1000                                                                           250 90            100                                    100                   63                                 100                                         16                                 90                                      __________________________________________________________________________ 

What is claimed is:
 1. A compound of the formula: ##STR24## in which R¹ represents cyclohexyl; R* represents dichlorophenyl or a group of the formula: ##STR25## wherein R² represents methoxy, chloro, fluoro, or trifluoromethyl, m represents 1 or 2, and X represents, when m is 1, halogen, triazolyl, --OCOR⁶, --SSCNR⁷ R⁸, or --SCH₂ COOR⁶ wherein R⁶ represents alkyl and R⁷ and R⁸ independently represent lower alkyl; or X represents oxygen when m is
 2. 2. A pesticidal composition which comprises as an essential component the compound of the formula (I) as defined in claim 1 together with a suitable carrier or adjuvant. 